An anthroxozole derivative and use thereof

Abstract

The application belongs to the technical field of organic electroluminescent materials, and particularly relates to an anthroxazole derivative and application thereof. The structural general formula of the anthroxazole derivative is shown as formula (I). When the anthroxazole derivative is applied to an organic electroluminescent element as a material of a carrier transport layer, the organic electroluminescent element can realize high efficiency, low driving voltage and long service life because the carrier mobility of the anthroxazole derivative is larger than that of previous materials, the anthroxazole derivative has excellent amorphousness, and the thin film state of the anthroxazole derivative is stable.

Description

TECHNICAL FIELD

[0001] The present application belongs to the technical field of organic electroluminescent materials, and particularly relates to an anthraoxazole derivative and application thereof. BACKGROUND

[0002] An organic electroluminescent diode (OLED) is also called an organic electroluminescent device, which is a technology that organic materials emit light under the action of an electric field through carrier injection and recombination. It can convert electric energy into light energy through organic light-emitting materials, including passive driving OLED (PMOLED) and active driving OLED (AMOLED). OLED is a new generation of display technology after cathode ray tube (CRT) and liquid crystal display (LCD), and is called dreamlike display technology. OLED also shows good development prospects in the field of communication terminals, military and flexible display. However, compared with other display technologies, OLED has a short development time, and the theoretical system of organic electroluminescent display technology is still not comprehensive and systematic. This field is full of opportunities and challenges, such as low device efficiency, high production requirements and cost, short device life and poor stability, which still need to be solved.

[0003] One of the key factors affecting the efficiency of OLED devices is the injection and recombination process of carriers in the device. Research has found that the device efficiency can be effectively improved by balancing the carriers. However, the balance of carriers is difficult to control, which affects the exciton recombination luminescence of the light-emitting layer, resulting in low device efficiency. It is currently believed that the hole transport rate in OLED devices is much higher than the electron transport rate, so developing electron transport materials with high transport rate is an effective way to improve the light-emitting efficiency of the device, which has important research significance. Some common electron transport materials, such as metal organic complexes, have good film-forming properties and excellent electron transport performance. Quinoline materials have low reduction potential, good mechanical properties and high thermal stability. Triazine compounds have excellent heat resistance and high electron affinity. Oxadiazole molecules have excellent chemical stability, high electron transport rate, low starting voltage, and good thermal stability.

[0004] Oxadiazole and oxadiazole have similar structures and both have electron-deficient properties, but electron transport materials of oxadiazole are not common. The oxadiazole structure has not been paid attention to in optoelectronic materials. Previously, it was found that the performance of oxadiazole as an electron transport material could be studied by functional modification, which filled the research blind spot of oxadiazole as an electron transport material and laid a foundation for future research work.

[0005] In view of the above reasons, the present application is proposed. SUMMARY

[0006] The purpose of this invention is to provide an anthraxazole derivative and its application. When the anthraxazole derivative is used as a carrier transport layer material in organic electroluminescent devices, the organic electroluminescent devices can achieve high efficiency, low driving voltage, and long lifetime because the anthraxazole derivative has a higher carrier mobility than conventional materials, excellent amorphous properties, and stable thin film state.

[0007] To achieve the above objectives, the present invention adopts the following technical solution:

[0008] An anthracoxazole derivative, the general structural formula of which is shown in formula (I):

[0009]

[0010] in,

[0011] R 1 ~R 6 Each is independently chosen from hydrogen, deuterium, cyano, halogen atom, substituted or unsubstituted C1-C. 30 Alkyl, substituted or unsubstituted C3-C 30 Cycloalkyl, substituted or unsubstituted C6-C 50 Aryl, substituted or unsubstituted C2-C 50 heteroaryl, substituted or unsubstituted C6-C 50 arylamine, substituted or unsubstituted C1-C 30 Alkyl silyl, substituted or unsubstituted C5-C 50 Arylsilyl or *—(L) n NAr 3 Ar 4 A group consisting of any two or more adjacent R groups 1 ~R 6 They can be arbitrarily joined or fused to form substituted or unsubstituted rings, and the formed rings may optionally contain one or more additional N, O, S, P, B, Si or Se heteroatoms;

[0012] L is selected from C6 to C6, which may be a free single bond, substituted, or unsubstituted. 50 aryl, substituted or unsubstituted C2-C 50 Groups composed of heteroaryl groups;

[0013] n represents an integer from 0 to 5;

[0014] Ar 1 Ar 2 Ar 3 Ar 4 Each time it appears, it is independently selected from substituted or unsubstituted C6 to C6. 50 Aryl, substituted or unsubstituted C2-C50 heteroaryl, substituted or unsubstituted C6-C 50 Groups composed of aryl amino groups;

[0015] *— indicates R 1 ~R 6 The connection key with equation (I).

[0016] Furthermore, the R 1 ~R 6 Each is independently selected from hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetraphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrene, substituted or unsubstituted triphenylene, substituted or unsubstituted anthraquinone, substituted or unsubstituted benzo[a]anthraquinone, substituted or unsubstituted pyrene, substituted or unsubstituted... Substituents, substituted or unsubstituted perylene, substituted or unsubstituted fluoranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted indolyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted triazine, or *—(L) n NAr 3 Ar 4 A group consisting of [groups].

[0017] Furthermore, the Ar 1 Ar 2 Ar 3 Ar 4 Each of the following is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted tetraphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrene, substituted or unsubstituted triphenylene, substituted or unsubstituted anthraquinone, substituted or unsubstituted benzo[a]anthraquinone, substituted or unsubstituted pyrene, substituted or unsubstituted [a] The group consisting of alkyl, substituted or unsubstituted perylyl, substituted or unsubstituted fluoranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted indolyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothiophene.

[0018] Furthermore, the R 1 ~R 6each independently selected from the group consisting of hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, or *—(L) m Het consisting of;

[0019] Ar 1 , Ar 2 each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, or *—(L) m Het consisting of;

[0020] m represents an integer of 0 to 5;

[0021] Het is selected from the group consisting of C2-C 50 heteroaryl;

[0022] *— represents R 1 ~ R 6 or Ar 1 , Ar 2 and the bond to Formula (I).

[0023] The alkyl used in the present application means a monovalent functional group obtained by removing one hydrogen atom from a straight chain or branched chain saturated hydrocarbon having 1 to 40 carbon atoms. As non-limiting examples thereof, there are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, isopentyl, hexyl, etc.;

[0024] The aryl in the sense of the present application contains 6 to 60 carbon atoms, and the heteroaryl contains 2 to 60 carbon atoms and at least one heteroatom, provided that the total of the carbon atoms and the heteroatoms is at least 5; the heteroatom is preferably selected from N, O or S. At this time, two or more rings of the heteroaryl can be simply attached to each other or attached in a condensed form, and further, can contain a form condensed with aryl. As non-limiting examples of the aryl and the heteroaryl, there are particularly selected from the following groups: phenyl, naphthyl, anthryl, benzanthryl, phenanthryl, pyrenyl, the group consisting of a pyrenyl group, a perylenyl group, a fluoranthenyl group, a tetracenyl group, a pentacenyl group, a benzopyrenyl group, a biphenyl group, a benzophenyl group, a terphenyl group, a trimesityl group, a tetraphenyl group, a fluorenyl group, a spirobifluorenyl group, a dihydronaphthyl group, a triphenylene group, a dihydropyrenyl group, a tetrahydropyrenyl group, a cis- or trans-indenofluorenyl group, a cis- or trans-indenocarbazolyl group, an indolocarbazolyl group, a benzofuranocarbazolyl group, a benzothiophenocarbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an azadibenzo[g, i d]naphtho[2, 1, 8-cde]azulene group, a truxenyl group, an isotruxenyl group, a spirotruxenyl group, a spiroisotruxenyl group, a furanyl group, a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a thiophenyl group, a benzothiophenyl group, an isobenzothiophenyl group, a dibenzothiophenyl group, a pyrrolyl group, an indolyl group, an isoindolyl group, a carbazolyl group, a pyridyl group, a quinolyl group, an isoquinolyl group, an acridyl group, a phenanthridyl group, a benzo[5, 6]quinolyl group, a benzo[6, 7]quinolyl group, a benzo[7, 8]quinolyl group, a phenothiazinyl group, a phenoxazinyl group, a pyrazolyl group, an indazolyl group, an imidazolyl group, a benzimidazolyl group, a naphthimidazolyl group, a phenanthimidazolyl group, a pyridimidazolyl group, a pyrazimidazolyl group, a quinoximidazolyl group, an oxazolyl group, a benzoxazolyl group, a naphthoxazolyl group, an anthroxazolyl group, a phenanthoxazolyl group, an isoxazolyl group, a 1, 2-thiazolyl group, a 1, 3-thiazolyl group, a benzothiazolyl group, a pyridazinyl group, a hexaazatriphenylene group, a benzopyridazinyl group, a pyrimidinyl group, a benzopyrimidinyl group, a quinoxalinyl group, a 1, 5-diazaanthryl group, a 2, 7-diazapyrenyl group, a 2, 3-diazapyrenyl group, a 1, 6-diazapyrenyl group, a 1, 8-diazapyrenyl group, a 4, 5-diazapyrenyl group, a 4, 5, 9, 10-tetraazaperylenyl group, a pyrazinyl group, a phenoxazinyl group, a phenothiazinyl group, a fluorubinyl group, a naphthidinyl group, an azacarbazolyl group, a benzocarbolinyl group, a carbolinyl group, a phenanthrolinyl group, a 1, 2, 3-triazolyl group, a 1, 2, 4-triazolyl group, a benzotriazolyl group, a 1, 2, 3-oxadiazolyl group, a 1, 2, 4-oxadiazolyl group, a 1, 2, 5-oxadiazolyl group, a 1, 3, 4-oxadiazolyl group, a 1, 2, 3-thiadiazolyl group, a 1, 2, 4-thiadiazolyl group, a 1, 2, 5-thiadiazolyl group, a 1, 3, 4-thiadiazolyl group, a 1, 3, 5-triazinyl group, a 1, 2, 4-triazinyl group, a 1, 2, 3-triazinyl group, a tetrazolyl group, a 1, 2, 4, 5-tetrazinyl group, a 1, 2, 3, 4-tetrazinyl group, a 1, 2, 3, 5-tetrazinyl group, a purinyl group, a pteridinyl group, an indolizinyl group, a quinazolinyl group, a benzothiadiazolyl group, or a group derived from a combination of these systems.

[0025] As used herein, "halogen" or "halo" means fluorine, chlorine, bromine, or iodine.

[0026] As used herein, heteroalkyl refers to an alkyl group in which one or more hydrogen atoms have been replaced with a heteroatom selected from the group consisting of halogen, nitrile, N, O, S, or Si. As non-limiting examples, there are difluoromethyl, trifluoromethyl, trifluoroethyl, pentafluoroethyl, nitrile, acetonitrile, methoxymethyl, methoxyethyl, trimethylsilyl, triisopropylsilyl, and the like. As used herein, haloalkyl refers to an alkyl group in which one or more hydrogen atoms have been replaced with a halogen. As non-limiting examples, there are fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, trifluoroethyl, pentafluoroethyl, and the like.

[0027] As used herein, alkenyl or alkynyl groups contain at least two carbon atoms. As non-limiting examples, alkenyl or alkynyl groups are preferably considered to mean cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, or octynyl.

[0028] As used herein, alkoxy or alkylthio groups preferably having 1 to 40 carbon atoms are considered to mean methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, t-butoxy, n-pentoxy, sec-pentoxy, 2-methylbutoxy, n-hexoxy, cyclohexoxy, n-heptoxy, cycloheptoxy, n-octoxy, cyclooctoxy, 2-ethylhexoxy, pentafluoroethoxy, 2,2,2-trifluoroethoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, t-butylthio, trifluoromethylthio, pentafluoroethylthio, 2,2,2-trifluoroethylthio, vinyloxy, vinylthio, propenyloxy, propenylthio, butenylthio, butenyloxy, pentoenyloxy, pentoenylthio, cyclopentoenyloxy, cyclopentoenylthio, hexenyloxy, hexenylthio, cyclohexenyloxy, cyclohexenylthio, ethynyloxy, ethynylthio, propynyloxy, propynylthio, butynyloxy, butynylthio, pentyloxy, pentoenylthio, hexenyloxy, hexynylthio.

[0029] Generally, the cycloalkyl, cycloalkenyl groups according to the present application can be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, cycloheptenyl, in which one or more -CH2- groups can be replaced by N, O, or S to form heterocycloalkyl, heterocycloalkenyl groups, for example, one -CH2- group in cyclopentyl is replaced by O to form tetrahydrofuranyl, one -CH2- group in cyclohexyl is replaced by O to form tetrahydropyranyl, and the like; in addition, one or more hydrogen atoms can also be replaced by a deuterium atom, a halogen atom, or a nitrile group.

[0030] As used herein, aryloxy refers to R'O -The monovalent functional group represented by R' is an aryl group having 6 to 60 carbon atoms. As non-limiting examples of such aryloxy groups, there are phenoxy, naphthoxy, biphenyloxy, and the like.

[0031] The arylthio group used in the present application means a group represented by R"S - The monovalent functional group represented by R" is an aryl group having 6 to 60 carbon atoms. As non-limiting examples of such arylthio groups, there are phenylthio, naphthylthio, biphenylthio, and the like.

[0032] The alkylsilyl group used in the present application means a silyl group substituted with an alkyl group having 1 to 40 carbon atoms, and the number of carbon atoms constituting the alkylsilyl group is at least 3. As non-limiting examples of alkylsilyl groups, there are trimethylsilyl, triethylsilyl, and the like. The arylsilyl group means an alkylsilyl group substituted with at least one aryl group having 6 to 60 carbon atoms. As non-limiting examples, there are phenyldimethylsilyl, naphthyldimethylsilyl, phenyldiethylsilyl, diphenylmethylsilyl, diphenylethylsilyl, triphenylsilyl, and the like.

[0033] The "alkylcarbonyl", "alkoxycarbonyl", "arylcarbonyl", "arylboronyl", "alkylboronyl" in the present application means a substituted carbonyl group (-COR*), wherein R* is preferably selected from the group consisting of alkyl, alkoxy, cycloalkyl, aryl, heteroaryl, arylboron, alkylboron.

[0034] The arylphosphine group used in the present application means a diarylphosphine group substituted with an aryl group having 6 to 60 carbon atoms. As non-limiting examples of arylphosphine groups, there are diphenylphosphine, di(4-trimethylsilylphenyl)phosphine, and the like. The aryloxyphosphine group is a diarylphosphine group in which the phosphorus atom is oxidized to the highest valence state.

[0035] The arylboron group used in the present application means a diarylboron group substituted with an aryl group having 6 to 60 carbon atoms. As non-limiting examples of arylboron groups, there are diphenylboron, di(2,4,6-trimethylphenyl)boron, and the like. The alkylboron group means a dialkylboron group substituted with an alkyl group having 1 to 40 carbon atoms. As non-limiting examples of alkylboron groups, there are di-t-butylboron, di-isobutylboron, and the like.

[0036] The arylalkyl group according to the present application means an alkyl group in which at least one hydrogen atom of a straight-chain or branched-chain saturated hydrocarbon having 1 to 40 carbon atoms is substituted with an aryl group having 6 to 60 carbon atoms. As non-limiting examples, there are phenylmethyl, diphenylmethyl, triphenylmethyl, 2-phenylethyl, 3-phenylpropyl, and the like.

[0037] Alkyl aryl according to the present application means an aryl group in which at least one hydrogen atom of an aryl group having from 6 to 60 carbon atoms is substituted with a linear or branched saturated hydrocarbon group having from 1 to 40 carbon atoms, and as non-limiting examples, methylphenyl, dimethylphenyl, trimethylphenyl, t-butylphenyl, isopropylphenyl, and the like can be mentioned.

[0038] As preferred, the heteroaryl group is, at each occurrence, independently selected from the group consisting of the following groups II-1 to II-13:

[0039]

[0040] wherein,

[0041] Z1, Z2are each independently selected from the group consisting of hydrogen, deuterium, halogen, hydroxyl, nitrile, nitro, amino, amidine, hydrazine, hydrazone, carboxyl or carboxylate salt thereof, sulfonic acid group or sulfonate salt thereof, phosphoric acid group or phosphate salt thereof, C1-C 40 alkyl, C2-C 40 alkenyl, C2-C 40 alkynyl, C1-C 40 alkoxy, C3-C 40 cycloalkyl, C3-C 40 cycloalkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 arylthioether, substituted or unsubstituted C6-C 60 aromatic amine, or substituted or unsubstituted C2-C 60 heteroaryl group;

[0042] x1represents an integer from 1 to 4; x2represents an integer from 1 to 3; x3represents 1 or 2; x4represents an integer from 1 to 6; x5represents an integer from 1 to 5;

[0043] T1represents O, S or NAr’;

[0044] Ar’ is selected from the group consisting of C1-C 40 alkyl, C1-C 40 heteroalkyl, C3-C 40 cycloalkyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 fused ring aryl, substituted or unsubstituted C6-C 60 aromatic amine, or substituted or unsubstituted C2-C 60 heteroaryl group; preferably, Ar’ is methyl, ethyl, phenyl, biphenyl or naphthyl;

[0045] a linking site of the represented group.

[0046] Further, the Het is selected from the group consisting of the groups represented by formulae II-1 to II-13.

[0047] As preferred, the term "substituted or unsubstituted" in the present application means that the group is substituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, C1-C 40 alkyl, C1-C 40 haloalkyl, C2-C 40 alkenyl, C2-C 40 alkynyl, C1-C 40 alkoxy, C1-C 40 alkylthio, C3-C 40 cycloalkyl, C3-C 40 cycloalkenyl, 3- to 7-membered heterocycloalkyl, C6-C 60 aryloxy, C6-C 60 arylthio, 3- to 30-membered heteroaryl unsubstituted or substituted with one or more C6-C 60 aryls, at least one of which is substituted with one or more C1-C 40 alkyl groups and one or more 3- to 30-membered heteroaryl groups, C6-C 60 aryl groups unsubstituted or substituted with one or more C1-C 40 alkylsilyl groups, C6-C 60 arylsilyl groups, C1-C 40 alkyl(C6-C 60 )arylsilyl groups, C1-C 40 alkyldi(C6-C 60 )arylsilyl groups, C1-C 40 alkylcarbonyl groups, C1-C 40 alkoxycarbonyl groups, C6-C 60 arylcarbonyl groups, di(C6-C 60 )arylboryl groups, di(C1-C 40 )alkylboryl groups, C1-C 40 alkyl(C6-C 60 )arylboryl groups, C6-C 60 aryl-substituted (C1-C 40 )alkyl groups, and C1-C 40 alkyl-substituted (C6-C 60 )aryl groups.

[0048] The arylene group in the present application refers to a divalent functional group obtained by removing two hydrogen atoms from an aromatic hydrocarbon having 6 to 60 carbon atoms. As non-limiting examples thereof, there are phenylene group, naphthylene group, phenanthrylene group, anthrylene group, fluorenylene group, spirobifluorenylene group, and the like.

[0049] The heteroarylene group or heteroarylene group in the present application refers to a divalent functional group obtained by removing two hydrogen atoms from a heteroaromatic hydrocarbon having 2 to 60 carbon atoms. As non-limiting examples thereof, there are pyridylene group, quinolylene group, isoquinolylene group, carbazolylene group, pyrimidinylene group, triazinylene group, and the like.

[0050] The arylene group or heteroarylene group according to the foregoing is linked to Het or N as a divalent functional group, and preferably, L is each independently selected from a single bond or a group consisting of the groups represented by III-1 to III-25 below, at each occurrence:

[0051]

[0052]

[0053] wherein X is selected from O, S, Se, CR’R”, SiR’R”, or NAr’;

[0054] Z 11 , Z 12 , Z 13 , Z 14 is each independently selected from the group consisting of hydrogen, deuterium, a halogen atom, a hydroxyl group, a nitrile group, a nitro group, an amino group, an amidine group, a hydrazine group, a hydrazone group, a carboxyl group or a carboxylate thereof, a sulfonic acid group or a sulfonate thereof, a phosphoric acid group or a phosphate thereof, a C1-C20alkyl group, a C2-C20alkenyl group, a C2-C20alkynyl group, a C1-C20alkoxy group, a C3-C20cycloalkyl group, a C3-C20cycloalkenyl group, a substituted or unsubstituted C6-C20aryl group, a substituted or unsubstituted C6-C20aryloxy group, a substituted or unsubstituted C6-C20arylthioether group, or a substituted or unsubstituted C2-C20heteroaryl group, at each occurrence; 60 60 60 60 60 60 60 60 60 60 at each occurrence;

[0055] y1 represents an integer of 1 to 4; y2 represents an integer of 1 to 6; y3 represents an integer of 1 to 3; y4 represents an integer of 1 to 5; y5 represents an integer of 1 or 2;

[0056] R’, R” are each independently selected from the group consisting of C1-C20alkyl group, C1-C20alkoxy group, C3-C20cycloalkyl group, C3-C20cycloalkenyl group, substituted or unsubstituted C6-C20aryl group, substituted or unsubstituted C6-C20aryloxy group, substituted or unsubstituted C6-C20arylthioether group, or substituted or unsubstituted C2-C20heteroaryl group, at each occurrence; 60 60 ​​​​​​​​​​heteroalkyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 Aromatic amino group, or substituted or unsubstituted C2-C 60 The group consisting of heteroaryl groups, R' and R" may optionally be joined or fused to form one or more additional substituted or unsubstituted rings, the formed rings containing or not containing one or more heteroatoms N, P, B, O or S; preferably, R' and R" are methyl, phenyl or fluorenyl;

[0057] Ar' chooses freely from C1 to C. 60 Alkyl, C1-C 60 heteroalkyl, C3-C 60 cycloalkyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 Fused aryl, substituted or unsubstituted C6-C 60 Aromatic amino group, or substituted or unsubstituted C2-C 60 The group consisting of heterocyclic aryl groups; preferably, Ar' is methyl, ethyl, phenyl, biphenyl, or naphthyl;

[0058] In this context, the dashed lines represent the bonding sites of functional groups.

[0059] Preferably, X is selected from O or S.

[0060] Preferably, each L is independently selected from a single bond or from the group consisting of groups shown in III-1 to III-15 and III-25.

[0061] Preferably, the Z 11 Z 12 Z 13 Z 14 Each group is independently selected from groups composed of hydrogen, deuterium, fluorine, and nitrile groups.

[0062] Furthermore, the anthracoxazole derivative is selected from one or more of the following E100 to E285 structures:

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072] wherein each *—G—* is independently selected from *—O—*, *—S—*, or one of the structures shown below:

[0073]

[0074] *— and —* represent a bond.

[0075] As used herein, "combination thereof' or "group" means that one or more members of the applicable list are combined to form a known or chemically stable arrangement that one of ordinary skill in the art would envision from the applicable list. For example, alkyl and deuterium atoms can be combined to form a partially or fully deuterated alkyl group; halogen and alkyl groups can be combined to form a haloalkyl substituent, such as trifluoromethyl, and the like; and halogen, alkyl, and aryl groups can be combined to form a haloaralkyl group.

[0076] An organic electroluminescent material including the anthrazoxole derivative.

[0077] The organic electroluminescent material can be composed of the anthrazoxole derivative of the present application alone, or can contain other compounds simultaneously.

[0078] The anthrazoxole derivative of the present application contained in the organic electroluminescent material of the present application can be used as, but not limited to, a light-emitting layer material, a carrier transport layer material, a capping layer, or a charge generation layer material.

[0079] An organic electroluminescent device including a first electrode, a second electrode, a capping layer, and at least one organic layer disposed between the first electrode and the second electrode, at least one of the organic layer and the capping layer comprising the anthrazoxole derivative provided by the present application.

[0080] The organic electroluminescent device comprises a cathode, an anode and at least one light-emitting layer. In addition to these layers, it can also comprise further layers, for example in each case one or more hole-injection layers, hole-transport layers, hole-blocking layers, electron-transport layers, electron-injection layers, exciton-blocking layers, electron-blocking layers and / or charge-generation layers. An interlayer with, for example, exciton-blocking function can likewise be introduced between two light-emitting layers. It should be noted, however, that not all of these layers need necessarily be present. The organic electroluminescent device described here can comprise one light-emitting layer, or it can comprise a plurality of light-emitting layers. A plurality of light-emitting compounds capable of emitting light are used in the light-emitting layer. Preference is given to a system having three light-emitting layers, wherein the three layers can exhibit blue, green and red emission. If more than one light-emitting layer is present, at least one of the layers according to the application comprises an anthroxazole derivative according to the application.

[0081] Further, the organic electroluminescent device according to the application does not comprise a separate hole-injection layer and / or hole-transport layer and / or hole-blocking layer and / or electron-transport layer, i.e. the light-emitting layer is directly adjacent to the hole-injection layer or the anode, and / or the light-emitting layer is directly adjacent to the electron-transport layer or the electron-injection layer or the cathode.

[0082] In the further layers of the organic electroluminescent device according to the application, in particular in the hole-transport layer and the capping layer and in the electron-transport layer, all materials can be used in the manner generally used according to the prior art. The person of ordinary skill in the art will thus be able to use all materials known for organic electroluminescent elements in combination with the light-emitting layer according to the application without inventive step.

[0083] Preference is furthermore given to an organic electroluminescent device which applies one or more layers by means of a sublimation method, wherein the material is applied in a vacuum sublimation apparatus at a pressure of less than 10 -5 Pa, preferably less than 10 -6 Pa. However, the initial pressure can also be lower, for example less than 10 -7 Pa.

[0084] Preference is likewise given to an organic electroluminescent device which applies one or more layers by means of an organic vapour phase deposition method or by means of carrier gas sublimation, wherein the material is applied at a pressure of between 10 -5 Pa and 1 Pa. A particular example of this method is the organic vapour jet printing method, wherein the material is applied directly through a nozzle and is thus structured.

[0085] It is furthermore preferred that the organic electroluminescent device is produced from solution, for example by spin coating, or by means of any desired printing method, such as screen printing, flexographic printing, offset printing, light-induced thermal imaging, thermal transfer, inkjet printing or nozzle printing. Soluble compounds, for example by suitable substitution of the fused-ring compounds of the formula I, are obtained. These methods are also particularly suitable for oligomers, dendrimers and polymers. It is furthermore possible to use hybrid methods, in which one or more layers are applied from solution and one or more further layers are applied by vapour deposition.

[0086] These methods are generally known to the person of ordinary skill in the art and they can apply them without inventive skill to organic electroluminescent elements comprising the fused-ring compounds according to the application.

[0087] The application therefore also relates to a method for producing an organic electroluminescent device according to the application, which applies at least one layer by means of a sublimation method, and / or at least one layer by means of an organic vapour phase deposition method or by means of carrier gas sublimation, and / or at least one layer from solution by spin coating or by means of a printing method.

[0088] Further, the present application relates to a compound of the present application as defined above. The same preferences as indicated above with regard to the organic electroluminescence device apply to the compound of the present application. In particular, the compound can further preferably comprise further compounds. Formulations of the compounds of the present application are required for processing the compounds of the present application from the liquid phase, for example by spin coating or by printing methods. These formulations can be, for example, solutions, dispersions or emulsions. For this purpose, mixtures of two or more solvents can be preferably used. Suitable and preferred solvents are, for example, toluene, anisole, o-xylene, m-xylene or p-xylene, methyl benzoate, mesitylene, tetralin, o-dimethoxybenzene, tetrahydrofuran, methyltetrahydrofuran, tetrahydropyran, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-)-fenchone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1 -methyl naphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methyl anisole, 4-methylanisole, 3,4-dimethylanisole, 3,5-dimethylanisole, acetophenone, alpha-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decalin, dodecylbenzene, ethyl benzoate, indane, methyl benzoate, 1 -methylpyrrolidone, p-cymene, phenetole, 1,4-diisopropylbenzene, benzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropyl naphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1,1 -bis(3,4-dimethylphenyl)ethane, or mixtures of these solvents.

[0089] Further, the organic layer is selected from one or several of an electron transport layer, a hole blocking layer, an electron blocking layer, a hole transport layer, a hole injection layer, a light emitting layer and a charge generation layer.

[0090] Further, the electron transport layer, the light emitting layer, the capping layer or the charge generation layer comprises an anthroxazole derivative of the present application.

[0091] Further, the light emitting layer comprises an anthroxazole derivative of the present application.

[0092] Further, the light emitting layer comprises a dopant and a light emitting host, the dopant comprising an anthracene, naphthalene, anthracene, pyrene, perylene, phenanthrene, fluoranthene, In addition to the above, as the dopant material, a pyrene derivative having a pyrene skeleton in the molecule, a heterocyclic compound having an indole ring as a partial structure of a condensed ring, a heterocyclic compound having a carbazole ring as a partial structure of a condensed ring, a carbazole derivative, a thiazole derivative, a benzimidazole derivative, a polydialkylfluorene derivative, quinacridone, coumarin, rubrene, perylene and derivatives thereof, a benzopyran derivative, indenophenanthrene derivative, rhodamine derivative, aminostyryl derivative, and the like can be used. They can be used as a single layer formed alone, as a single layer formed by mixing with other materials, or as a stacked structure between layers formed alone, between layers formed by mixing, or between a layer formed alone and a layer formed by mixing.

[0093] In addition, a phosphorescent emitter can also be used as the dopant. As the phosphorescent emitter, a phosphorescent emitter of a metal complex of iridium, platinum, or the like can be used. A green phosphorescent emitter such as Ir(ppy)3, a blue phosphorescent emitter such as Firpic, Fir6, a red phosphorescent emitter such as Btp2Ir(acac), and the like can be used, and as the host material at this time, a carbazole derivative of the present application is preferably used. In addition, as a hole-injection and -transporting host material (P-type material), a carbazole derivative such as 4,4'-di(N-carbazolyl)diphenyl (CBP), 4,4',4'-tris(carbazol-9-yl)triphenylamine (TCTA), 9,9'-(1,3-phenyl)di-9H-carbazole (mCP), and the like can be used. As an electron-transporting host material (n-type material), a carbazole derivative such as p-bis(triphenylsilyl)benzene (UGH2), 2,2',2"-(1,3,5-phenylene)-tris(1-phenyl-1H-benzimidazole) (TPBI), and the like can be used, and a high-performance light-emitting element can be produced.

[0094] In the case of doping of a phosphorescent light-emitting material into a host material, in order to avoid concentration quenching, doping is preferably performed by co-evaporation in a range of 1 to 10% by weight with respect to the light-emitting layer.

[0095] In addition, as the light-emitting dopant material, a material emitting delayed fluorescence such as 2-biphenyl-4,6-bis(12-phenylindolo[2,3-a]carbazol-11-yl)-1,3,5-triazine (PIC-TRZ), 9,9”-(6-phenyl-1,3,5-triazine-2,4-diyl)bis((9H-3,9’-bicarbazole)) (CC2TA), benzoxazin-2,4,6-triphenyl-1,3,5-triazine (PXZ-TRZ), 2,4,5,6-tetra(9-carbazolyl)-1,3,5-triazine (4CzIPN), and the like can also be used.

[0096] Further, the light-emitting host comprises the anthroxazole derivative of the present application.

[0097] Further, the mass ratio of the dopant to the light-emitting host is 1:99 to 50:50.

[0098] A consumer product made of the organic electroluminescent device, wherein the consumer product comprises the organic electroluminescent device provided by the present application.

[0099] The consumer product of the present application can be one of the following products: a flat panel display, a computer monitor, a medical monitor, a television, a signboard, a lamp for internal or external illumination and / or signaling, a head-up display, a fully or partially transparent display, a flexible display, a laser printer, a telephone, a cellular phone, a tablet computer, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro display with a diagonal less than 2 inches, a 3-D display, a virtual reality or augmented reality display, a vehicle, a video wall comprising a plurality of displays tiled together, a theater or stadium screen, a phototherapy device, and a signboard.

[0100] Compared with the prior art, the present application has the following advantages:

[0101] The anthroxazole derivative of the present application has a large planar conjugated anthroxazole novel rigid structure. For the compound represented by the general formula (I) of the present application, since it has the characteristics of (1) large carrier mobility, (2) high internal quantum efficiency, (3) stable thin film state, and (4) excellent heat resistance, it is suitable for use as a material constituting the light-emitting layer of the organic electroluminescent element of the present application.

[0102] For the organic electroluminescent element of the present application using the anthroxazole derivative represented by the above general formula (I) of the present application as the host material of the light-emitting layer, since a compound having large carrier mobility, high internal quantum efficiency, excellent amorphousness, and stable thin film state is used, an organic electroluminescent element with high efficiency, low driving voltage, and long lifetime can be achieved.

[0103] Further, in the present application, by forming a light-emitting layer with the anthranyloxadiazole derivative of the above general formula (I), the high quantum efficiency performance and heat resistance possessed by the compound can be maximally effectively utilized, and an organic electroluminescent element with a long lifetime can be realized with higher efficiency.

[0104] Further, in the present application, in the organic electroluminescent element of the present application using the anthranyloxadiazole derivative represented by the above general formula (I) as a constituent material in at least any one of the above light-emitting layer, or the stacked film of two or more light-emitting layers, since a compound having high carrier mobility, high internal quantum efficiency, and excellent amorphousness, and stable in a thin film state is used, an organic electroluminescent element with high efficiency, low driving voltage, and long lifetime can be realized. BRIEF DESCRIPTION OF DRAWINGS

[0105] In order to more clearly illustrate the technical solutions of the embodiments of the present application or the prior art, the following will briefly introduce the drawings needed to be used in the embodiments or prior art description. Obviously, the drawings in the following description are only some embodiments of the present application, and other drawings can also be obtained by those skilled in the art without any creative effort based on these drawings.

[0106] Figure 1 An organic light-emitting device 100 is shown schematically. The drawing is not necessarily drawn to scale. The device 100 can include a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light-emitting layer 106, a hole blocking layer 107, an electron transport layer 108, an electron injection layer 109, a cathode 110, and a capping layer (CPL) 111. The device 100 can be fabricated by sequentially depositing the described layers.

[0107] Figure 2 An organic light-emitting device 200 is shown schematically that exhibits two light-emitting layers. The device includes a substrate 201, an anode 202, a hole injection 203, a hole transport layer 204, a first light-emitting layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, a hole transport layer 209, a second light-emitting layer 210, an electron transport layer 211, an electron injection layer 212, and a cathode 213. The device 200 can be prepared by sequentially depositing the described layers. Because the most common OLED device has one light-emitting layer, and the device 200 has a first light-emitting layer and a second light-emitting layer, the light-emitting peaks of the first and second light-emitting layers can be overlapping or cross-overlapping or non-overlapping. In the corresponding layers of the device 200, similar materials to those described with respect to the device 100 can be used. Figure 2 One example of how to add some layers to the structure of the device 100 is provided. DETAILED DESCRIPTION

[0108] In order to make the objects, technical solutions and advantages of the present application clearer, the technical solutions of the present application will be described in detail below. Obviously, the described embodiments are only a part of the embodiments of the present application, rather than all the embodiments. Based on the embodiments of the present application, all other embodiments obtained by a person of ordinary skill in the art without creative work fall within the scope of protection of the present application.

[0109] In the present application, the preparation methods are all conventional methods unless otherwise specified. The raw materials used are all available from public commercial channels unless otherwise specified, and the percentages are all mass percentages unless otherwise specified. The series of novel organic compounds provided in the present application are all reacted under well-known suitable conditions, and some involve simple organic preparation, for example, the preparation of phenylboronic acid derivatives, which can be synthesized by skilled operation skills, and are not described in detail in the present application.

[0110] Any range recited in the present application includes the end values and any intervening values and any sub-range comprised of any such values.

[0111] The following examples describe the test instruments and methods for testing the performance of OLED materials and elements:

[0112] OLED element performance detection conditions:

[0113] Luminance and chromaticity coordinates: tested using a spectral scanner PhotoResearch PR-715;

[0114] Current density and turn-on voltage: tested using a digital source meter Keithley 2420;

[0115] Power efficiency: tested using a NEWPORT 1931-C;

[0116] Lifetime test: tested using a LTS-1004AC lifetime test device.

[0117] Example 1

[0118] The preparation method of compound E155 comprises the following steps:

[0119] First step: preparation of compound Int-1

[0120]

[0121] Under nitrogen protection, 20.0 mmol of 3-cyano-2-iodonaphthalene was dissolved in 110 mL of 1,2-dichloroethane, 22.0 mmol of NBS, 10.0 mmol of p-toluenesulfonic acid and 1.0 mmol of palladium acetate were added, and the reaction was stirred at 70°C for 12 hours. The reaction was cooled to room temperature, 50 mL of saturated aqueous sodium bisulfite was added, and the organic phase was separated. The aqueous phase was extracted with dichloromethane, and the organic phase was collected, dried, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain compound Int-1, a yellow solid, in a yield of 83%.

[0122] Step 2: Preparation of compound Int-2

[0123]

[0124] Under nitrogen protection, 20.0 mmol of Int-1 was dissolved in 80 mL of dry THF, and the reaction was stirred at 0°C for 1 hour. Then, 22.0 mmol of phenylmagnesium bromide in THF was added dropwise, and the reaction was stirred at room temperature for 1 hour. Then, 50 mL of 2M dilute hydrochloric acid aqueous solution was added, and the organic phase was separated. The aqueous phase was extracted with ethyl acetate, and the organic phase was collected, dried, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain compound Int-2, a yellow solid, in a yield of 85%.

[0125] Step 3: Preparation of compound Int-3

[0126]

[0127] Under nitrogen protection, 20.0 mmol of Int-2, 22.0 mmol of p-chlorobenzamidopropargyl and 60 mL of acetonitrile and 6 mL of triethylamine were mixed, and 1.0 mmol of cuprous iodide and 1.0 mmol of PdCl2(PPh3)2 catalyst were added. The reaction was stirred at reflux for 2 hours, and then cooled to room temperature. Then, 100 mL of saturated aqueous ammonium chloride solution was added, and the reaction was extracted with ethyl acetate. The organic phase was collected, dried, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain compound Int-3, a yellow solid, in a yield of 65%.

[0128] Step 4: Preparation of compound Int-4

[0129]

[0130] Int-3, 2.0 mmol of silver trifluoroacetate, 50 mL of 1,2-dichloroethane and 20.0 mmol of water were mixed under nitrogen protection, stirred at room temperature for 2 hours, then 40.0 mmol of p-toluenesulfonic acid was added, heated to 85°C and stirred for 1 hour, cooled to room temperature, 50 mL of saturated aqueous sodium bicarbonate solution was added, extracted with ethyl acetate, the organic phase was collected, dried, filtered, and the filtrate was concentrated under reduced pressure to dryness, and purified by silica gel column separation to obtain compound Int-4, yellow solid, yield: 62%.

[0131] Fifth step: preparation of compound Int-5

[0132]

[0133] Int-4 prepared in the previous step, 24.0 mmol of phenylboronic acid, 60.0 mmol of anhydrous sodium carbonate, 2.0 mmol of tetrabutylammonium bromide, 0.1 mmol of Pd(PPh3)4 and 60 mL of toluene were mixed under nitrogen protection, then 30 mL of ethanol and 30 mL of water were added, heated to reflux and stirred for 15 hours, cooled to room temperature, 50 mL of water was added, the organic phase was separated, the aqueous phase was extracted with toluene, the organic phase was dried, filtered, and the filtrate was concentrated under reduced pressure to dryness, and purified by silica gel column separation to obtain compound Int-5, yield 73%.

[0134] Sixth step: preparation of compound Int-6

[0135]

[0136] Int-5 prepared in the previous step and 2.0 mmol of p-toluenesulfonic acid were dissolved in 100 mL of dichloromethane under nitrogen protection, 22.0 mmol of NBS was added portionwise, stirred for 2 hours, 50 mL of water was added, the organic phase was separated, the aqueous phase was extracted with dichloromethane, the organic phase was dried, filtered, and the filtrate was concentrated under reduced pressure to dryness, and purified by silica gel column separation to obtain compound Int-6, yield 93%.

[0137] Seventh step: preparation of compound Int-7

[0138]

[0139] Referring to the synthesis method of the fifth step, only Int-4 was replaced by Int-6 to obtain compound Int-7, yield 84%.

[0140] Eighth step: preparation of compound Int-8

[0141]

[0142] Under nitrogen protection, 20.0 mmol of Int-7 prepared in the previous step, 24.0 mmol of pinacol diborane, 30.0 mmol of anhydrous potassium acetate, 2.0 mmol of cuprous iodide, 0.2 mmol of PdCl2(dppf), 0.4 mmol of XPhos and 80 mL of DMF were mixed, and the mixture was heated to 100°C and stirred for 15 hours, then cooled to room temperature. The reaction solution was poured into 150 mL of saturated aqueous sodium chloride solution, filtered, and the filter cake was washed with water and separated and purified on a silica gel column to obtain compound Int-8, white solid, yield 85%.

[0143] Ninth step: preparation of compound E950

[0144]

[0145] Under nitrogen protection, 22.0 mmol of Int-8 prepared in the previous step (reactant 1), 20.0 mmol of p-bromophenyl cyanide (reactant 2), 60.0 mmol of anhydrous sodium carbonate, 2.0 mmol of tetrabutylammonium bromide, 0.1 mmol of Pd(PPh3)4 and 60 mL of toluene solution were mixed, and then 30 mL of ethanol and 30 mL of water were added. The mixture was heated to reflux and stirred for 15 hours, then cooled to room temperature. 50 mL of water was added, and the organic phase was separated. The aqueous phase was extracted with toluene, and the organic phase was dried, filtered and concentrated under reduced pressure. The residue was dried and separated and purified on a silica gel column to obtain compound E155, yield 76%, MS (TOF): m / z 625.2218 [M+H] + , 1 HNMR (δ, CDC13): 8.22 (2H, s); 7.94-7.92 (2H, d); 7.84-7.80 (5H, m); 7.65-7.58 (4H, m); 7.54-7.46 (6H, m); 7.44-7.36 (5H, m); 7.26-7.24 (2H, d); 7.22-7.20 (2H, d).

[0146] Examples 2 to 102

[0147] The following compounds were prepared according to the synthetic method described above:

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159] Preparation of compound E238 of Example 103:

[0160]

[0161] Int-4' (reactant 1), 20.0 mmol of di([1,1'-biphenyl]-4-yl)amine (reactant 2), 30.0 mmol of sodium tert-butoxide and 60 mL of toluene were mixed under nitrogen protection, 0.2 mmol of Pd2(dba)3 catalyst and 0.4 mmol of Xantphos were added, the reaction was stirred at 110°C for 15 hours, cooled to room temperature, 50 mL of water was added, extracted with ethyl acetate, the organic phase was collected and dried, filtered, the filtrate was concentrated under reduced pressure and dried, separated and purified by silica gel column to obtain compound E238, yellow solid, yield 86%, MS (TOF): m / z 691.2763 [M+H] + , 1 HNMR (δ, CDC13): 8.51~8.49 (2H, d); 8.16~8.14 (2H, m); 7.82 (1H, s); 7.75~7.69 (4H, m); 7.66~7.60 (4H, m); 7.57~7.45 (12H, m); 7.42~7.36 (4H, m); 7.34~7.29 (4H, m); 7.15~7.11 (1H, m).

[0162] Examples 104 to 187

[0163] The following compounds were prepared by a synthetic method similar to the above-described examples:

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172] In the above embodiments, *—G—* is independently selected from *—O—*, *—S—*, or one of the structures shown below:

[0173]

[0174] *— and —* represent connector keys.

[0175] Application Examples 1 to 186

[0176] An OLED element 100, such as Figure 1 As shown, the OLED element in this embodiment is a top-emitting element, including a substrate 101, an anode layer 102 disposed on the substrate 101, a hole injection layer 103 disposed on the anode layer 102, a hole transport layer 104 disposed on the hole injection layer 103, an electron blocking layer 105 disposed on the hole transport layer 104, an organic light-emitting layer 106 disposed on the electron blocking layer 105, a hole blocking layer 107 disposed on the organic light-emitting layer 106, an electron transport layer 108 disposed on the hole blocking layer 107, an electron injection layer 109 disposed on the electron transport layer 108, a cathode 110 disposed on the electron injection layer 109, and a capping layer 111 above the cathode. The method for fabricating an OLED element that does not include the hole blocking layer 107 includes the following steps:

[0177] 1) The glass substrate coated with the ITO conductive layer was ultrasonically treated in the cleaning agent for 30 minutes, rinsed in deionized water, ultrasonically treated in the acetone / ethanol mixed solvent for 30 minutes, baked in a clean environment until completely dry, irradiated with a UV cleaner for 10 minutes, and bombarded with a low-energy cation beam.

[0178] 2) Place the prepared ITO glass substrate into a vacuum chamber and evacuate to a vacuum level less than 1 × 10⁻⁶. -5 Pa, metallic silver is deposited as the anode layer on the above ITO film, and the thickness of the deposited film is [missing information]. Compounds HI01 and HI02 were then deposited separately as hole injection layers, with HI02 accounting for 3% of the mass of HI01, and the deposited film thickness was [missing information].

[0179] 3) continue to evaporate compound HTM as a hole transport layer on the hole injection layer, the film thickness of the evaporated layer is

[0180] 4) continue to evaporate compound HT025 as an electron blocking layer on the hole transport layer, the film thickness of the evaporated layer is

[0181] 5) continue to evaporate the compound represented by formula (I) of the present application as a host material and RD030 as a dopant material on the electron blocking layer, wherein the mass ratio of RD030 to the compound represented by formula (I) is 5:100, as an organic light-emitting layer of the element, the film thickness of the obtained organic light-emitting layer is

[0182] 6) continue to evaporate a layer of LiQ and compound ET036 as an electron transport layer of the element on the organic light-emitting layer, wherein the mass ratio of compound ET036 to LiQ is 40:100, the film thickness of the evaporated layer is

[0183] 7) continue to evaporate a layer of LiF as an electron injection layer on the electron transport layer, the film thickness of the evaporated layer is

[0184] 8) evaporate metal magnesium and silver as a transparent cathode layer of the element on the electron injection layer, the mass ratio of magnesium to silver is 1:10, the film thickness of the evaporated layer is

[0185] 9) continue to evaporate a layer of HTM as a CPL layer of the element on the transparent cathode layer, the film thickness of the evaporated layer is to obtain the OLED element provided by the present application.

[0186] The structures of the compounds used in the above application examples are as follows:

[0187]

[0188] Application Example 187

[0189] An organic electroluminescent element 200, the structure of which is as shown in Figure 2 , comprises a substrate 201, an anode 202, a hole injection layer 203, a hole transport layer 204, a first light-emitting layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, a hole transport layer 209, a second light-emitting layer 210, an electron transport layer 211, an electron injection layer 212, and a cathode 213. The electroluminescent element 200 is prepared by a preparation method similar to that of Example 6.

[0190] Comparative Example 1

[0191] Following the same steps as in Application Example 1, replace the compound formula shown in (I) of the present invention in step 5) with E02 to obtain Comparative Element 1;

[0192]

[0193] Under the same brightness, the driving voltage, current efficiency, and lifetime of the organic electroluminescent elements prepared in Application Examples 1-186, Application Example 187, and Comparative Example 1 were measured using a digital source meter and a luminance meter. Specifically, the voltage was increased at a rate of 0.1V per second, and the measurement was performed when the brightness of the organic electroluminescent element reached 1000 cd / m². 2 The voltage at that time is the driving voltage, and the current density at that time is measured simultaneously; the ratio of brightness to current density is the current efficiency; the LT90% lifespan test is as follows: using a luminance meter at 1000 cd / m² 2 At a constant current under the given brightness, the brightness decay of the organic electroluminescent element was measured to be 900 cd / m². 2 Time is expressed in hours. All results are summarized in Table 1 and normalized to the test data of Comparative Example 1 (data in parentheses) for comparison.

[0194] Table 1 Performance test results of each component

[0195]

[0196]

[0197]

[0198]

[0199]

[0200] Where Me is methyl; Ph is phenyl; PhPh is biphenyl; and Nap is naphthyl.

[0201] The compounds of the present invention, when used as materials for the light-emitting layer, yielded high-efficiency and long-life organic electroluminescent devices. These devices exhibited low driving voltage, high current efficiency, and an excellent LT90% lifetime, demonstrating that the compounds of the present invention are high-performance organic electroluminescent materials.

[0202] The compound E02 in the comparative example 1 is compared with the compound of the present application, the difference is that the electronic transmission capacity of the phenanthrooxazole of E02 is weaker than the hole transmission capacity after introducing triarylamine group, which causes the unbalance of the exciton transmission in the element, the driving voltage of the element is increased, and the efficiency is reduced. The compound of the present application enhances the planar conjugation after introducing the substituent group to the anthrooxazole mother nucleus, and improves the electronic transmission capacity, so that the exciton transmission performance is greatly improved, the exciton transmission in the element is more balanced, and the element performance is significantly improved.

[0203] The organic electroluminescent device of the present application can be applied in the light emitting body of wall-mounted television, flat panel display, lighting, etc., the light source of copying machine, printer, backlight source of liquid crystal display, or metering instrument, display panel, identification lamp, etc.

[0204] The above is only a specific embodiment of the present application, but the protection scope of the present application is not limited to this, any person skilled in the art can easily think of changes or replacements within the technical range disclosed by the present application, which should be covered in the protection scope of the present application. Therefore, the protection scope of the present application should be subject to the protection scope of the claims.

Claims

1. An anthracoxazole derivative, characterized in that, The anthracoxazole derivative is selected from one or more of the following structures E100 to E285: ； ； ； ； ； ； ； ； ； ； Wherein, *—G—* is independently selected from *—O—*, *—S—*, or one of the structures shown below: 、 、 、 、 、 、 、 、 、 、 、 、 ； *— and —* represent connector keys.

2. An organic electroluminescent material, characterized in that, The organic electroluminescent material includes the anthracoxazole derivative as described in claim 1.

3. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes a first electrode, a second electrode, a capping layer, and at least one organic layer disposed between the first electrode and the second electrode, wherein at least one of the organic layer and the capping layer comprises the anthraquinone derivative of claim 1.

4. The organic electroluminescent device according to claim 3, characterized in that, The organic layer includes a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a charge generation layer; any one of the organic layers can be one, two, or multiple layers.

5. The organic electroluminescent device according to claim 4, characterized in that, At least one of the light-emitting layer, electron transport layer, capping layer and charge generation layer comprises the anthraquinone derivative of claim 1.

6. An organic electroluminescent product, characterized in that, The organic electroluminescent device comprising any one of claims 3 to 5.

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