Heterocyclic compounds and uses thereof

Abstract

The application relates to the technical field of organic electroluminescent materials, in particular to a heterocyclic compound and application thereof. The structural formula of the heterocyclic compound is shown as formula (I); the compound shown as formula (I) provided by the application has two imidazole structures. The compound is applied in an organic electroluminescent element, so that the driving voltage can be remarkably reduced, and the luminous efficiency and the service life are improved.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of organic electroluminescent materials, in particular to a heterocyclic compound and application thereof in an organic light-emitting element. BACKGROUND

[0002] Generally, the organic light-emitting phenomenon refers to a phenomenon that light is emitted when electric energy is applied to an organic substance; that is, when an organic layer is disposed between an anode and a cathode, if a voltage is applied between the two electrodes, holes are injected from the anode to the organic layer, and electrons are injected from the cathode to the organic layer; when the injected holes and electrons meet, an exciton is formed, and when the exciton transitions to a ground state, light and heat are emitted.

[0003] In recent years, the organic electroluminescent display technology has become mature, and some products have entered the market, but there are still many problems to be solved in the process of industrialization. In particular, various organic materials used for making elements, the carrier injection and transport performance, material electroluminescence performance, service life, color purity, matching between various materials and between each electrode, etc., still have many problems that have not been solved; in particular, the substances applied to the electron injection layer and the transport layer, as the earliest report related to the electron transport material, the representative electron transport layer substances such as oxadiazole derivatives, triazole derivatives, phenanthroline derivatives and imidazole groups described in patents CN107573328A, CN107556310A, CN113801066A, CN113429395A, CN113429348A, CN114560872A, etc., contain N-phenylbenzimidazole in their structures, in terms of function, not only have the ability to transport electrons, but also have the function of blocking holes from the light-emitting layer, but there is a problem of low thermal stability when applied to actual elements.

[0004] Therefore, in order to overcome the technical problems as described above and further improve the characteristics of the organic electroluminescent element, the development of more stable and effective substances that can be used as electron injection and transport substances in the organic electroluminescent element is continuously required.

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

[0006] The present application aims to provide a heterocyclic compound that can improve the thermal stability and the ability to transport carriers of the material, and an organic electroluminescent element prepared using the heterocyclic compound, which can significantly reduce the driving voltage, improve the luminous efficiency and the lifetime; another object of the present application is to provide the application of the compound.

[0007] Specifically, the present application provides the following technical solutions:

[0008] The present application provides a kind of heterocyclic compound, its structural formula is as shown in formula (I):

[0009]

[0010] Wherein,

[0011] L 1 、L 2 Each independently selected from the group consisting of single bond, substituted or unsubstituted C6-C 60 arylene, or substituted or unsubstituted C2-C 60 heteroarylene;

[0012] X 1 、X 2 、X 3 、X 4 、X 5 、X 6 Each independently represents CR 1 or N;

[0013] G represents O, S, SO, SO2, Se, CR 2 R 3 , SiR 2 R 3 or NAr 3 ;

[0014] R 1 , R 2 , R 3 Each independently selected from the group consisting of hydrogen, deuterium, fluorine, nitrile group, substituted or unsubstituted C1-C 40 alkyl, substituted or unsubstituted C1-C 40 alkoxy, substituted or unsubstituted C2-C 40 alkenyl, substituted or unsubstituted C1-C 40 alkylthio, substituted or unsubstituted C1-C 40 alkoxy, substituted or unsubstituted C3-C 40 cycloalkyl, substituted or unsubstituted C1-C 40 alkylsulfoxide, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 arylthio, substituted or unsubstituted C6-C 60 arylsulfoxide, substituted or unsubstituted C3-C 40 silyl, substituted or unsubstituted boron group, substituted or unsubstituted amine group, substituted or unsubstituted aryl phosphine group, substituted or unsubstituted phosphine oxide group, or substituted or unsubstituted C2-C 60a substituted or unsubstituted C6-Ci0aryl group, a substituted or unsubstituted C2-Ci0heteroaryl group, or a substituted or unsubstituted C3-Ci0cycloalkyl group;

[0015] Ar 1 , Ar 2 , Ar 3 each independently selected from the group consisting of a substituted or unsubstituted C6-Ci0aryl group, a substituted or unsubstituted C2-Ci0heteroaryl group, or a substituted or unsubstituted C3-Ci0cycloalkyl group; 60 a substituted or unsubstituted C6-Ci0aryl group, a substituted or unsubstituted C2-Ci0heteroaryl group, or a substituted or unsubstituted C3-Ci0cycloalkyl group; 60 a substituted or unsubstituted C6-Ci0aryl group, a substituted or unsubstituted C2-Ci0heteroaryl group, or a substituted or unsubstituted C3-Ci0cycloalkyl group; 60 a substituted or unsubstituted C6-Ci0aryl group, a substituted or unsubstituted C2-Ci0heteroaryl group, or a substituted or unsubstituted C3-Ci0cycloalkyl group; 60 a substituted or unsubstituted C6-Ci0aryl group, a substituted or unsubstituted C2-Ci0heteroaryl group, or a substituted or unsubstituted C3-Ci0cycloalkyl group.

[0016] In the substituted or unsubstituted ring formed by the combination of the adjacent groups in the present application, the "ring" means a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring. The condensed ring means a condensed aliphatic ring, a condensed aromatic ring, a condensed aliphatic heterocyclic ring, a condensed aromatic heterocyclic ring, or a combination thereof.

[0017] The heterocyclic compound according to the present application is represented by the above formula (I), wherein a heterocyclic ring such as a benzofuroquinoline, a benzofurophenanthroline, a benzothienoquinoline, a benzothienophenanthroline, or the like is bonded to form a basic skeleton via L 1 , L 2 In the present application, the compound represented by formula (I) is not only electrochemically stable and excellent in electron mobility, but also has a high glass transition temperature and excellent thermal stability, as compared with a heterocyclic structure such as a benzofuran, a benzothienoquinoline, or a phenanthroline. Thus, the heterocyclic compound of the present application is excellent in electron transportability and light emitting properties, and is useful as a material for any one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a hole blocking layer of an organic material layer of an organic electroluminescent element. It is preferable to be used as a material for any one of a light emitting layer, an electron transport layer, and an electron transport auxiliary layer which is stacked on the electron transport layer, and it is more preferable to be used as a material for an electron transport layer or an electron transport auxiliary layer.

[0018] Specifically, the compound of formula (I) of the present application has a stronger electron transport ability than a heterocycle such as dibenzofuran, dibenzothiophene, etc. having a weak electron-withdrawing group ability, by containing a quinoline or phenanthroline heterocycle, and thus can exhibit relatively high luminous efficiency and a high glass transition temperature. Thus, in the case where the heterocycle compound of formula (I) of the present application is used in an organic electroluminescent element, not only excellent thermal stability, carrier transport ability, electron transport ability, and light emitting ability can be obtained, but also the driving voltage of the element can be reduced, the efficiency and lifetime can be improved, and the like, and as a new electron transport layer material, an excellent efficiency increase due to a high triplet energy level can be exhibited.

[0019] Further, the heterocycle compound of formula (I) of the present application can have a wide band gap by adjusting the HOMO and LUMO energy levels according to the kind of the substituent group by introducing various substituents R 1 , Ar 1 , Ar 2 in the basic skeleton, and thus can exhibit high electron transportability in an organic electroluminescent element using such a compound.

[0020] Further, the heterocycle compound of formula (I) of the present application can have a high glass transition temperature by introducing various substituents L 1 , L 2 , and Ar 1 , Ar 2 , especially aryl and / or heteroaryl, to the above basic skeleton, and thus has a higher thermal stability than conventional light emitting materials such as phenanthroline. Thus, the performance and lifetime characteristics of an organic electroluminescent element containing the compound according to the present application can be greatly improved. The organic electroluminescent element having such improved performance and lifetime characteristics can ultimately maximize the performance of a full-color organic light emitting panel.

[0021] The heterocycle compound of formula (I) of the present application is preferably selected from the group consisting of the following structures:

[0022]

[0023] wherein the meanings of the symbols used are the same as defined above.

[0024] The aryl group in the sense of the present application contains 6 to 60 carbon atoms, the heteroaryl group contains 2 to 60 carbon atoms and at least one heteroatom, with the proviso that the sum of carbon atoms and heteroatoms is at least 5; the heteroatom is preferably selected from N, O or S. At this point, two or more rings of the heteroaryl group can be attached to each other simply or in condensed form, further, it can also contain a condensed form with aryl group. As non-limiting examples of such heteroaryl group, one can cite six-membered monocyclic such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; polycyclic such as phenoxazinyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazolyl, carbazolyl; and 2-furyl, N-imidazolyl, 2-isoxazolyl, 2-pyridyl, 2-pyrimidyl, etc.

[0025] Further, the aryl group, heteroaryl group or heterocyclic aryl group is preferably selected from the group consisting of phenyl, naphthyl, anthryl, benzanthryl, phenanthryl, pyrenyl, alkyl, peryl, fluoranyl, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, azophenyl, terphenyl, trimerphenyl, tetraphenyl, fluorenyl, spirodifluorenyl, dihydrophenanthrene, triphenylene, dihydropyrene, tetrahydropyrene, cis or trans indo[a]fluorenyl, cis or trans indo[a]carbazoyl, indole[a]carbazoyl, benzo[a]furan[a]carbazoyl, benzo[a]thio[a]carbazoyl, benzo[a]carbazoyl, dibenzo[a]carbazoyl, azadibenzo[g,ij]naphtho[2,1,8-cde]azine, trimerinyl, isotrimerinyl, spirotrimerinyl, spiroisotrimerinyl, furanyl, benzo[a]furanyl, isobenzo[a]furanyl Dibenzofuranyl, thiophenyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, pyrroleyl, indoleyl, isoindoleyl, carbazoyl, pyridyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, benzo[5,6]quinolinyl, benzo[6,7]quinolinyl, benzo[7,8]quinolinyl, phenothiazinyl, phenotoxazinyl, pyrazolyl, indazoleyl, imidazoleyl, benzimidazoleyl, naphthimazoleyl, phenanthimazoleyl, pyridiniumimazoleyl, pyraziniumimazoleyl, quinoxoliniumimazoleyl, oxazolyl, benzoxoxazolyl, naphthoxazolyl, anthraquinonexazolyl, phenanthoxazolyl, isoxazolyl, 1,2- Thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, hexaazabenzophenanthryl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthrayl, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenoxazinyl, phenthiazinyl, fluoresceinyl, naphridinyl, azacarbazolyl, benzocarbaolinyl, carbaolinyl, phenanthrolinel, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1 The group consisting of or derived from the group consisting of 2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetraazinyl, 1,2,3,4-tetraazinyl, 1,2,3,5-tetraazinyl, purine, pteridine, indazinyl, quinazolinyl, and benzothiadiazolyl.

[0026] Furthermore, the R 1 R 2 R 3 Each is independently selected from the group consisting of hydrogen, deuterium, methyl, substituted or unsubstituted phenyl, and substituted or unsubstituted fluorene.

[0027] Furthermore, G is selected from O or S.

[0028] Furthermore, the X1 For N and / or X 1 ~X 6 For CR 1 .

[0029] Furthermore, the Ar 1 Ar 2 Ar 3 Each of the following groups, selected independently with or without substitution, consists of: phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthryl, pyrene, etc. alkyl, perylene, fluoranyl, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, azophenyl, terphenyl, trimerphenyl, tetraphenyl, fluorenyl, spirodifluorenyl, dihydrophenanthrene, triphenylene, dihydropyrene, tetrahydropyrene, cis or trans indo[a]fluorenyl, cis or trans indo[a]carbazoyl, indole[a]carbazoyl, benzo[a]furan[a]carbazoyl, benzo[a]thio[a]carbazoyl, benzo[a]carbazoyl, dibenzo[a]carbazoyl, azadibenzo[g,ij]naphtho[2,1,8-cde]azine, trimerinyl, isotrimerinyl, spirotrimerinyl, spiroisotrimerinyl, furanyl, benzo[a]furanyl, isobenzofuran , dibenzofuranyl, thiophenyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, pyrroleyl, indoleyl, isoindoleyl, carbazoyl, pyridinyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, benzo[5,6]quinolinyl, benzo[6,7]quinolinyl, benzo[7,8]quinolinyl, phenothiazinyl, phenotoxazinyl, pyrazolyl, indazoleyl, imidazoyl, benzimidazoleyl, naphthiazoleyl, phenanthiazoleyl, pyridiniumimidazoyl, pyraziniumimidazoyl, quinoxoliniumimidazoyl, oxazolyl, benzoxoxazolyl, naphthiazoleyl, anthraquinonexazolyl, phenanthiazoleyl, isoxazolyl, 1 2-Thiazolyl, 1,3-Thiazolyl, benzothiazolyl, pyridazinyl, hexaazabenzophenanthryl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthrayl, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenoxazinyl, phenthiazinyl, fluoresceinyl, naphridinyl, azacarbazolyl, benzocarbaolinyl, carbaolinyl, phenanthrolinel, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazinyl Azolium, 1,2,3-oxadiazolium, 1,2,4-oxadiazolium, 1,2,5-oxadiazolium, 1,3,4-oxadiazolium, 1,2,3-thiadiazolium, 1,2,4-thiadiazolium, 1,2,5-thiadiazolium, 1,3,4-thiadiazolium, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolium, 1,2,4,5-tetraazinyl, 1,2,3,4-tetraazinyl, 1,2,3,5-tetraazinyl, purine, pteridine, indazinyl, quinazolinyl, benzothiadiazolium, or groups derived from combinations of these systems.

[0030] According to embodiments of the present application, the R 1 is selected from hydrogen, deuterium, fluorine or nitrile group.

[0031] Further, the heteroaryl or heterocyclic aryl group is selected from the group consisting of the following groups II-1 to II-17:

[0032]

[0033]

[0034] wherein,

[0035] Z1, Z2are each independently selected from the group consisting of hydrogen, deuterium, halogen, hydroxyl, nitrile group, nitro group, amino group, amidine group, hydrazine group, hydrazone group, carboxyl group 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 group, or substituted or unsubstituted C5-C 60 heterocyclic aryl group;

[0036] 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;

[0037] T1represents O, S, CR’R” or NAr’;

[0038] R’, R” are each independently selected from the group consisting of hydrogen, deuterium, C1-C 40 alkyl, C1-C 40 heteroalkyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 arylamino, or substituted or unsubstituted C5-C 60 heterocyclic aryl group; R’ and R” can optionally join or fuse to form one or more additional substituted or unsubstituted rings, with or without one or more heteroatoms N, P, B, O or S in the formed ring; preferably, R’, R” are methyl, phenyl or fluorenyl;

[0039] Ar’ is selected from the group consisting of C1-C40 Alkyl groups, C1-C 40 heteroalkyl, C3-C 40 cycloalkyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 Fused aryl groups, substituted or unsubstituted C6-C 60 Aromatic amino groups, or substituted or unsubstituted C5-C 60 The group consisting of heterocyclic aryl groups; preferably, Ar' is methyl, ethyl, phenyl, biphenyl, or naphthyl;

[0040] Indicates the location of the bond.

[0041] Furthermore, the Ar 1 Ar 2 Ar 3 Each of the following groups, selected independently with or without substitution, consists of: phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthryl, pyrene, etc. fluorenyl, spirobifluorenyl, dihydronaphthyl, triphenylenyl, dihydropyranyl, tetrahydropyranyl, cis- or trans-indenofluorenyl, cis- or trans-indenocarbazolyl, indolocarbazolyl, benzofuranocarbazolyl, benzothiophenocarbazolyl, benzocarbazolyl, dibenzocarbazolyl, azadibenzo[g, ij]naphtho[2,1,8-cde]azulene, triindenyl, isotriindenyl, spirotrindenyl, spiroisotriindenyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, indolyl, isoindolyl, carbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo[5,6]quinolyl, benzo[6,7]quinolyl, benzo[7,8]quinolyl, phenoxathiinyl, phenoxazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthimidazolyl, phenanthroimidazolyl, pyridimidazolyl, pyrazimidazolyl, quinoximidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthroxazolyl, phenanthroxazolyl, isoxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, hexaazatriphenylene, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthryl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperylenyl, pyrazinyl, phenoxazinyl, phenothiazinyl, fluorubinyl, naphthidinyl, azacarbazolyl, benzocarbolinyl, carbolinyl, phenanthrolinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetrazinyl, 1,2,3,4-tetrazinyl, 1,2,3,5-tetrazinyl, purinyl, pteridinyl, indolizinyl, quinazolinyl, benzothiadiazolyl, or a group derived from a combination of these systems.

[0042] In the heterocyclic compound of formula (I) of the present application, L 1 , L 2 is a functional group for connecting the above-mentioned heterocyclic skeleton containing a benzofuranquinoline, benzofuranphenanthroline, benzothiophenquinoline, benzothiophenphenanthroline, and the above-mentioned Ar 1 , Ar 2 may be selected from a single bond, a C6-C 60 arylene group, and a C2-C60 group. In this case, as preferable, the L 1 , L 2 are each independently selected from a single bond or a group consisting of the following III-1 to III-23:

[0043]

[0044] wherein the dotted line represents a bonding site of the group, and in this case, the bonding position of the group represented by the above formula III-1 to III-23 is not limited to ortho, meta or para. The above L 1 , L 2 may each independently be substituted by one or more selected from the group consisting of deuterium, a halogen atom, a nitrile group, a C1-C 40 alkyl group, a C6-C 60 aryl group and a C2-C 60 heteroaromatic group, and in this case, when the substituents are plural, the plural substituents are preferably the same as or different from each other.

[0045] In the present application, the term "substituted or unsubstituted" means that one or more substituents selected from the group consisting of hydrogen, deuterium, a halogen atom, a hydroxyl group, a nitrile group, a nitro group, an amino group, an amidino 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-C 40 alkyl group, a C2-C 40 alkenyl group, a C2-C 40 alkynyl group, a C1-C 40 alkoxy group, a C3-C 40 cycloalkyl group, a C3-C 40 cycloalkenyl group, a C6-C 60 aryl group, a C6-C 60 aryloxy group, a C6-C 60 aryl sulfide group and a C2-C 60 heteroaromatic group, or substituted with a substituent in which two or more of the above exemplified substituents are linked.

[0046] An alkyl group in the sense of the present application contains 1 to 40 carbon atoms and is a straight-chain alkyl group or an alkyl group having a branch, which is individually substituted or not; an alkenyl group or an alkynyl group contains at least two carbon atoms, and as non-limiting examples, alkyl, alkenyl or alkynyl groups are preferably considered to mean methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, t-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, cyclopentyl, n-hexyl, neohexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl.

[0047] Alkoxy preferably having 1 to 40 carbon atoms is considered to mean methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, t-butoxy, n-pentoxy, sec-pentoxy, 2-methylbutoxy, n-hexyloxy, cyclohexyloxy, n-heptyloxy, cycloheptyloxy, n-octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy and 2,2,2-trifluoroethoxy.

[0048] Heteroalkyl preferably having 1 to 40 carbon atoms is considered to mean a group in which a single hydrogen atom or -CH2- group is replaced by an oxygen, sulfur, halogen atom, as non-limiting examples, alkoxy, alkylthio, fluorinated alkoxy, fluorinated alkylthio, particularly methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, t-butoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, t-butylthio, trifluoromethylthio, trifluoromethoxy, pentafluoroethoxy, pentafluoroethylthio, 2,2,2-trifluoroethoxy, 2,2,2-trifluoroethylthio, vinyloxy, vinylthio, propenyloxy, propenylthio, butenylthio, butenyloxy, pentenyloxy, pentenylthio, cyclopentenyloxy, cyclopentenylthio, hexenyloxy, hexenylthio, cyclohexenyloxy, cyclohexenylthio, ethynoxy, ethynylthio, propynoxy, propynylthio, butynoxy, butynylthio, pentynoxy, pentynylthio, hexynoxy, hexynylthio.

[0049] Generally, the cycloalkyl group, the cycloalkenyl group 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 the above-mentioned groups; furthermore, one or more hydrogen atoms can also be replaced by a deuterium atom, a halogen atom or a nitrile group.

[0050] The heterocycloalkyl group used in the present application is a monovalent functional group obtained by removing one hydrogen atom from a non-aromatic hydrocarbon having an atomic number of 3 to 40. At this time, one or more carbons in the ring, preferably 1 to 3 carbons, are replaced by a heteroatom such as N, O or S. As non-limiting examples thereof, there are tetrahydrofuran, tetrahydrothiophene, morpholine, piperazine and the like.

[0051] The fused ring aryl group used in the present application is a monovalent functional group obtained by removing one hydrogen atom from an aromatic hydrocarbon having 6 to 60 carbon atoms in which two or more rings are combined. At this time, the two or more rings can be simply attached to each other or attached in a condensed form. As non-limiting examples thereof, there are, for example, phenanthryl, anthryl, fluoranthenyl, pyrenyl, triphenylenyl, perylenyl,

[0052] ​The arylamine group used in the present application means an amine substituted with an aryl group having 6 to 60 carbon atoms. Non-limiting examples of the arylamine group include diphenylamine group, N-phenyl-1-naphthylamine group, N-(1-naphthyl)-2-naphthylamine group, and the like. The heteroarylamine group used in the present application means an amine substituted with an aryl group having 6 to 60 carbon atoms and a heteroaryl group having 2 to 60 carbon atoms. Non-limiting examples of the heteroarylamine group include N-phenylpyridin-3-amine group, N-([1,1'-biphenyl]-4-yl)dibenzo[b,d] furan-2-amine group, N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine group, and the like.

[0053] The alkoxy group used in the present application means an RO - monovalent functional group represented by the formula, and the R is an alkyl group having 1 to 40 carbon atoms, which can include a linear, branched, or cyclic structure. Non-limiting examples of such an alkoxy group include methoxy group, ethoxy group, n-propoxy group, 1-propoxy group, t-butoxy group, n-butoxy group, pentoxy group, cyclopentoxy group, cyclohexyloxy group, and the like.

[0054] The aryloxy group used in the present application means an R'O - monovalent functional group represented by the formula, and the R' is an aryl group having 6 to 60 carbon atoms. Non-limiting examples of such an aryloxy group include phenoxy group, naphthoxy group, biphenyloxy group, and the like.

[0055] The alkylsilyl group used in the present application means a silyl group substituted with an alkyl group having 1 to 40 carbon atoms. The number of carbon atoms constituting the alkylsilyl group is at least 3. Non-limiting examples of the alkylsilyl group include trimethylsilyl group, triethylsilyl group, and the like. The arylsilyl group means a silyl group substituted with an aryl group having 6 to 60 carbon atoms.

[0056] The arylphosphine group used in the present application means a diarylphosphine group substituted with an aryl group having 6 to 60 carbon atoms. Non-limiting examples of the arylphosphine group include diphenylphosphine group, di(4-trimethylsilylphenyl)phosphine group, and the like. The aryloxyphosphine group means a diarylphosphine group in which the phosphorus atom is oxidized to the highest valence state.

[0057] The arylboron group used in the present application means a diarylboron group substituted with an aryl group having 6 to 60 carbon atoms. Non-limiting examples of the arylboron group include diphenylboron group, di(2,4,6-trimethylphenyl)boron group, and the like. The alkylboron group means a dialkylboron group substituted with an alkyl group having 1 to 40 carbon atoms. Non-limiting examples of the alkylboron group include di-t-butylboron group, di-isobutylboron group, and the like.

[0058] Preferably, the heterocyclic compound is selected from the group consisting of compounds represented by the following formulae J544 to J660:

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065] wherein T is selected from O, S, SO, Se, CMe2, CPh2, NPh, NPhPh;

[0066] X is selected from O or S;

[0067] Me represents methyl, Ph represents phenyl, and PhPh represents biphenyl.

[0068] The present application also provides an organic electroluminescent material, the raw material of which comprises the heterocyclic compound described above; the organic electroluminescent material comprising the heterocyclic compound of the present application has the ability of carrier transport.

[0069] The present application also provides the use of the heterocyclic compound described above in the production of an organic electroluminescent element.

[0070] The present application also provides an organic electroluminescent element, which comprises: a first electrode, a second electrode, a capping layer, and one or more organic layers disposed between the first electrode and the second electrode; the material of at least one of the organic layers or the capping layer comprises the heterocyclic compound described above.

[0071] The organic electroluminescent element 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 intermediate layer having, for example, an exciton-blocking function can likewise be introduced between two light-emitting layers. It should be noted, however, that not all of these layers necessarily have to be present. The organic electroluminescent device described here can comprise one light-emitting layer, or it can comprise a plurality of light-emitting layers. That is to say, a plurality of light-emitting compounds capable of emitting light are used in the light-emitting layer. A system having three light-emitting layers is particularly preferred, wherein the three layers can display blue, green and red emission. If there is more than one light-emitting layer, at least one of these layers comprises, according to the application, the heterocyclic compound of the present application.

[0072] Further, the organic electroluminescent element according to the present application does not comprise a separate hole injection layer and / or a hole transport layer and / or a hole blocking layer and / or an electron transport layer, i.e. the emission layer is directly adjacent to the electron blocking layer or the hole transport layer or the anode, and / or the emission layer is directly adjacent to the electron transport layer or the electron injection layer or the cathode.

[0073] In the other layers of the organic electroluminescent element according to the present application, in particular in the hole injection and hole transport layers and in the electron injection and electron transport layers, 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 emission layer according to the present application without inventive step.

[0074] Further preferred is an organic electroluminescent element, wherein one or more layers are applied 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 even lower, for example less than 10 -7 Pa.

[0075] Also preferred is an organic electroluminescent element, wherein one or more layers are applied 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.

[0076] Further preferred is an organic electroluminescent element, wherein one or more layers are produced from solution, for example by spin coating, or by means of any desired printing method, for example screen printing, flexographic printing, offset printing, light-induced thermal imaging, thermal transfer, inkjet printing or nozzle printing. Solubility of the compounds is obtained, for example, by suitable substitution. These methods are also particularly suitable for oligomers, dendrimers and polymers. Further possible is a hybrid method, wherein one or more layers are applied from solution and one or more further layers are applied by vapour deposition.

[0077] These methods are generally known to the person of ordinary skill in the art and he can apply them to an organic electroluminescent element comprising a compound according to the present application without inventive step.

[0078] The application therefore also relates to a method for producing an organic electroluminescent element according to the application, at least one layer being applied by means of a sublimation method, and / or at least one layer being applied by means of an organic vapour phase deposition method or by means of carrier gas sublimation, and / or at least one layer being applied from solution by spin coating or by means of a printing method.

[0079] Furthermore, the application relates to at least one heterocyclic compound according to the application as indicated above. The same preferences as indicated above in connection with the organic electroluminescent element apply to the compounds according to the application. In particular, the heterocyclic compounds can preferably also comprise further compounds. For the processing of the heterocyclic compounds according to the application from the liquid phase, for example by spin coating or by means of a printing method, formulations of the compounds according to the application are required. These formulations can be, for example, solutions, dispersions or emulsions. For this purpose, mixtures of two or more solvents can preferably be used. Suitable and preferred solvents are, for example, toluene, anisole, o-, m- 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-methylanisole, 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, dibenzyl 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.

[0080] As a preference, the organic layer comprises a hole injection layer, a hole transport layer, a hole blocking layer, an emission layer, an electron transport layer, an electron injection layer or an electron blocking layer.

[0081] The present application also provides a consumer product comprising the organic electroluminescent element described above. The consumer product described in the present application can be one of the following devices: a flat panel display, a computer monitor, a medical monitor, a television, a billboard, a lamp for interior or exterior illumination and / or signaling, a heads-up display, a full or partial transparent display, a flexible display, a laser printer, a telephone, a cellular phone, a tablet, 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 sign.

[0082] In addition, unless otherwise specified, the raw materials used in the present application can be purchased from a commercial supplier, and any range recited in the present application includes the end value, any number between the end values, and any sub-range comprised of any combination of the end values or the numbers between the end values.

[0083] The present application has the following advantages:

[0084] The heterocyclic compound represented by formula (I) provided by the present application is excellent in electron mobility, thermal stability, and light emission properties, and can be applied to an organic layer of an organic electroluminescent element. In particular, in the case where the heterocyclic compound represented by formula (I) of the present application is used for an electron transport layer and an electron transport auxiliary layer, an organic electroluminescent element having a lower driving voltage, higher efficiency, and longer lifetime than conventional electron transport materials can be manufactured, and furthermore, a full-color display panel having improved performance and lifetime can be manufactured. BRIEF DESCRIPTION OF DRAWINGS

[0085] 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, an organic 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 manufactured by sequentially depositing the described layers.

[0086] Figure 2An organic light emitting device 200 showing two light emitting layers is schematically illustrated. The device includes 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 device 200 can be prepared by sequentially depositing the described layers. Since the most common OLED device has one light emitting layer, while the device 200 has a first light emitting layer and a second light emitting layer, the light emission peaks of the first light emitting layer and the second light emitting layer 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 from the structure of the device 100 is provided. DETAILED DESCRIPTION

[0087] The following examples are intended to illustrate the present application but not to limit the scope of the present application.

[0088] In the description of the present application, unless otherwise specified, the meaning of "a plurality of" is two or more; the terms "upper", "lower", and the like indicate the orientation or positional relationship shown in the drawings based on the orientation or positional relationship shown in the drawings, and are only used to facilitate the description of the present application and simplify the description, and do not indicate or imply that the indicated device or element must have a particular orientation, be constructed and operated in a particular orientation, and therefore cannot be understood as a limitation on the present application.

[0089] The experimental methods used in the following examples are conventional methods unless otherwise specified. The experimental materials and related equipment used in the following examples, unless otherwise specified, can be obtained commercially, and the percentages, unless otherwise specified, are mass percentages.

[0090] The following examples describe the test instruments and methods for testing the performance of OLED materials and elements:

[0091] OLED element performance detection conditions:

[0092] Luminance and chromaticity coordinates: tested using a spectral scanner PhotoResearch PR-715;

[0093] Current density and turn-on voltage: tested using a digital source meter Keithley 2420;

[0094] Power efficiency: tested using a NEWPORT 1931-C.

[0095] Example 1

[0096] The preparation method of compound J569, taken X = O as an example, includes the following steps:

[0097] First step: preparation of intermediate Int-1

[0098]

[0099] Referring to the synthesis method disclosed in Org. Lett., 2021, 23, 9526-9532, 20.0 mmol of sub-1, 24.0 mmol of sub-2 were dissolved in 50 mL of 1,2-dichloroethane under nitrogen protection, and 40.0 mmol of trifluoromethanesulfonic acid was added. The temperature was raised to 90°C, and the reaction was stirred for 10 hours. After cooling to room temperature, the reaction solution was concentrated under reduced pressure and dried. Purification was performed by silica gel column separation to obtain compound Int-1, white solid, yield: 66%.

[0100] Second step: preparation of intermediate Int-2

[0101]

[0102] Under nitrogen protection, 20.0 mmol of Int-1 prepared in the previous step, 80.0 mmol of anhydrous potassium carbonate and 60 mL of DMF were mixed, and the temperature was raised to 125°C. The reaction was stirred for 5 hours, and then cooled to room temperature. The reaction solution was poured into 150 mL of ice water, filtered, and the filter cake was washed with water and recrystallized with methanol to obtain compound Int-2, white solid, yield 87%.

[0103] Third step: preparation of intermediate Int-3

[0104]

[0105] 20.0 mmol of Int-2 prepared in the previous step was dissolved in 100 mL of xylene, and 2.0 g of 10% palladium / carbon was added. The temperature was raised to reflux and the reaction was stirred for 15 hours. After cooling to room temperature, the mixture was filtered, the filter cake was washed with dichloromethane, and the filtrate was concentrated under reduced pressure and dried. Purification was performed by silica gel column separation to obtain compound Int-3, white solid, yield 92%.

[0106] Fourth step: preparation of intermediate Int-4

[0107]

[0108] 20.0 mmol of Int-3 prepared in the previous step was dissolved in 50 mL of dichloromethane, and 22.0 mmol of N-bromosuccinimide was added portionwise. The reaction was stirred at room temperature for 2 hours, 50 mL of water was added, and the organic phase was separated and washed with water three times. The organic phase was dried, filtered, and the filtrate was concentrated under reduced pressure and dried to obtain compound Int-4, yellow solid, yield 100%.

[0109] Step 5: Preparation of intermediate Int-5

[0110]

[0111] Under nitrogen protection, 20.0 mmol of Int-4 prepared in the previous step was dissolved in 50 mL of dry THF, and cooled to -78 °C. 24.0 mmol of 2.5 M n-butyllithium n-hexane solution was added dropwise, and the reaction was stirred for 10 minutes. 25.0 mmol of trimethyl borate was added dropwise, and the reaction was stirred for 30 minutes. The temperature was raised to room temperature, and the reaction was stirred for 1 hour. 20 mL of 3M dilute hydrochloric acid was added dropwise, and the organic phase was separated. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined, washed with saturated brine, dried, filtered, and the filtrate was concentrated under reduced pressure to dryness. 20 mL of n-hexane was added to the residue, which was filtered, and the filter cake was washed with n-hexane to obtain compound Int-5, a yellow solid, in a yield of 84%.

[0112] Step 6: Preparation of compound J569

[0113]

[0114] Under nitrogen protection, 22.0 mmol of Int-5 prepared in the previous step, 20.0 mmol of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine, and 60 mL of toluene were mixed, and 60.0 mmol of anhydrous potassium carbonate, 0.02 mmol of Pd(PPh3)4 catalyst, 30 mL of water, and 30 mL of ethanol were added. The reaction was stirred at reflux for 15 hours, and the temperature was lowered to room temperature. 50 mL of water was added, and the organic phase was separated. The aqueous phase was extracted with dichloromethane, and the organic phases were combined, dried, filtered, and the filtrate was concentrated under reduced pressure to dryness. Purification was performed using a silica gel column, and recrystallization was performed using dichloromethane / ethanol to obtain compound J569 (X = O), a white solid, in a yield of 85%, MS (TOF) m / z: 653.2281 [M+H]; 1 HNMR (δ, CDC13): 8.48 (1H, s); 8.38-8.34 (4H, m); 8.14-8.12 (2H, m); 7.96-7.94 (2H, m); 7.91-7.89 (1H, d); 7.85-7.82 (2H, m); 7.80-7.74 (2H, m); 7.71-7.67 (1H, m); 7.56-7.47 (8H, m); 7.45-7.38 (3H, m); 7.26-7.24 (2H, m).

[0115] The compound with X=S was prepared according to the similar synthetic method described above, except that sub-2 of the first step was replaced with 2-(2,2-difluoro-l- ((trimethylsilyl)oxy)vinyl)benzenethiol, white solid, yield 81%, MS (TOF) m / z: 669.2047 [M+H] ; 1 HNMR (δ, CDC13): 8.48 (1H, s); 8.38-8.34 (4H, m); 8.14-8.09 (4H, m); 8.01-7.99 (1H, d); 7.97-7.95 (2H, m); 7.83-7.81 (1H, d); 7.75-7.69 (2H, m); 7.56-7.47 (8H, m); 7.45-7.38 (3H, m); 7.26-7.24 (2H, m).

[0116] Examples 2 to 93

[0117] The following compounds shown in Table 1 were prepared according to the similar synthetic method described above:

[0118] Table 1

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127] Example 94

[0128] The preparation method of compound J653, taken X=O as an example, comprises the following steps:

[0129] First Step: Preparation of Intermediate Int-6

[0130]

[0131] Under nitrogen protection, 20.0 mmol of sub-3, 24.0 mmol of sub-4 were dissolved in 50 mL of 1,2-dichloroethane, 40.0 mmol of trifluoromethanesulfonic acid was added, and the temperature was raised to 90°C. The reaction was stirred for 10 hours, cooled to room temperature, concentrated under reduced pressure, and dried. Purification was performed by silica gel column separation to obtain compound Int-6, yellow solid, yield: 68%.

[0132] Second step: preparation of intermediate Int-7

[0133]

[0134] Referring to the synthesis method of the second step of Example 1, only Int-1 of the second step of Example 1 was replaced by Int-6 to prepare compound Int-7, yellow solid, yield 89%.

[0135] Third step: preparation of intermediate Int-8

[0136]

[0137] 20.0 mmol of Int-7 prepared in the previous step was dissolved in 100 mL of xylene, 0.1 mol of manganese dioxide was added, the temperature was raised to reflux, and the reaction was stirred for 15 hours. After cooling to room temperature, filtration was performed, the filter cake was washed with dichloromethane, the filtrate was concentrated under reduced pressure and dried, and purification was performed by silica gel column separation to obtain compound Int-8, yellow solid, yield 95%.

[0138] Fourth step: preparation of intermediate Int-9

[0139]

[0140] Under nitrogen protection, 20.0 mmol of Int-8 prepared in the previous step was dissolved in 60 mL of DMF, 24.0 mmol of pinacol diboronic acid, 30.0 mmol of anhydrous potassium acetate, 2.0 mmol of cuprous iodide, and 0.2 mmol of catalyst PdCl2(dppf)CH2Cl2 were added, the temperature was raised to 100°C, and the reaction was stirred for 15 hours. After cooling to room temperature, 150 mL of ice water was added, filtration was performed, the filter cake was washed with water, and the solid was purified by silica gel column separation to obtain compound Int-9, yellow solid, yield 86%.

[0141] Fifth step: preparation of compound J653

[0142]

[0143] Under nitrogen protection, 22.0 mmol of Int-9 prepared in the previous step, 20.0 mmol of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine and 60 mL of toluene were mixed, 60.0 mmol of anhydrous potassium carbonate, 0.02 mmol of Pd(PPh3)4 catalyst, 30 mL of water and 30 mL of ethanol were added, the reaction was stirred at elevated temperature and refluxed for 15 hours, it was cooled to room temperature, 50 mL of water was added, the organic phase was separated, the aqueous phase was extracted with dichloromethane, the combined organic phases were dried, filtered, the filtrate was concentrated under reduced pressure and dried, it was purified by silica gel column separation and recrystallized with dichloromethane / ethanol to obtain compound J653 (X=O), yellow solid, yield 86%, MS (TOF) m / z: 654.2234 [M+H]; 1 HNMR (δ, CDC13): 9.08 (1H, s); 8.48-8.45 (1H, m); 8.38-8.34 (4H, m); 8.14-8.12 (1H, d); 8.03-8.01 (1H, d); 7.98-7.96 (2H, m); 7.83-7.80 (2H, m); 7.75 (1H, s); 7.57-7.49 (7H, m); 7.45-7.38 (5H, m); 7.26-7.24 (2H, m).

[0144] The compound of X=S was prepared according to the similar synthesis method described above, only sub-4 in the first step was replaced by 5-chloro-2-(2,2-difluoro-1-((trimethylsilyl)oxy)vinyl)benzenethiol, yellow solid, yield 84%, MS (TOF) m / z: 670.2001 [M+H]; 1 HNMR (δ, CDC13): 9.08 (1H, s); 8.48-8.45 (1H, m); 8.38-8.34 (4H, m); 8.25-8.20 (2H, m); 8.18-8.12 (2H, m); 7.98-7.96 (2H, m); 7.82-7.81 (1H, d); 7.58-7.50 (7H, m); 7.45-7.38 (5H, m); 7.26-7.24 (2H, m).

[0145] Examples 95-117

[0146] The following compounds shown in Table 2 were prepared according to the similar synthesis method described above:

[0147] Table 2

[0148]

[0149]

[0150]

[0151] In the above embodiments, X is O or S; T is selected from O, S, CMe2, CPh2, NPh, NPhPh;

[0152] Me stands for methyl, Ph for phenyl, and PhPh for biphenyl.

[0153] Example 118

[0154] An OLED element, such as Figure 1 As shown, the OLED element in this embodiment is a top-emitting element, including a substrate 101, an anode 102 disposed on the substrate 101, a hole injection layer 103 disposed on the anode 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:

[0155] 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.

[0156] 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 on the above ITO film, and the thickness of the deposited film is [missing information]. HI01 and F4TCNQ were then deposited separately as hole injection layers, with F4TCNQ accounting for 3% of the mass of HI01, and the deposited film thickness was [missing information].

[0157] 3) The compound HTM is then deposited onto the aforementioned hole injection layer as a hole transport layer, with a deposition thickness of [missing information].

[0158] 4) Further depositing the compound EBL as an electron blocking layer on the aforementioned hole transport layer, with a film thickness of [missing information].

[0159] 5) RH020 as the host material and RD011 as the dopant material are further deposited on the electron blocking layer. RD011 accounts for 3% of the mass of RH020. This forms the organic light-emitting layer of the device. The thickness of the deposited organic light-emitting layer is [missing information].

[0160] 6) continue to evaporate a layer of LiQ and the compound of formula (I) of the present application on the organic light-emitting layer as an electron transport layer, wherein the compound of formula (I) of the present application is 50% of the mass of LiQ, and the evaporation film thickness is 100 A.

[0161] 7) continue to evaporate a layer of LiF on the electron transport layer as an electron injection layer, and the evaporation film thickness is 10 A.

[0162] 8) evaporate a layer of metal magnesium and silver on the electron injection layer as a transparent cathode layer of the element, the mass ratio of magnesium and silver is 1:10, and the evaporation film thickness is 1000 A.

[0163] 9) continue to evaporate a layer of CPD on the transparent cathode layer as a CPL layer of the element, and the evaporation film thickness is 100 A. An OLED element provided by the present application is obtained.

[0164] The structure of the compound used in the above-mentioned example 118 is as follows:

[0165]

[0166] Example 119

[0167] 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.

[0168] Comparative Example 1

[0169] According to the same procedure as in example 118, the compound of formula (I) of the present application in step 6) is replaced by E01 to obtain comparative element 1.

[0170]

[0171] The organic electroluminescent element prepared by the above process is subjected to the following performance tests:

[0172] The driving voltage and current efficiency of the organic electroluminescent element prepared in example 118, 119 and comparative example 1, and the service life of the element are measured using a digital source meter and a luminance meter. Specifically, the voltage is increased at a rate of 0.1 V per second, and the driving voltage at which the luminance of the organic electroluminescent element reaches 1000 cd / m 2The voltage at this time is the driving voltage, and the current density at this time is measured simultaneously; the ratio of the brightness to the current density is the current efficiency; the LT95% lifetime test is as follows: using a luminance meter to maintain a constant current at 1000 cd / m 2 The brightness of the organic electroluminescent element is measured to be 950 cd / m 2 The time is in hours. The data listed in Table 3 are relative data compared with Comparative Element 1.

[0173] Table 3

[0174]

[0175]

[0176]

[0177] As can be seen from Table 3, the element prepared from the heterocyclic compound of the present application has a lower driving voltage, a significantly improved current efficiency, and a 1.23-fold improvement over the comparative element at the same brightness, and the LT95% lifetime of the element is also improved, indicating that the heterocyclic compound of the present application is an excellent electron transport layer material.

[0178] The compound E01 in Comparative Example 1 differs from the compound of the present application in that E01 has a larger axial steric hindrance, resulting in a higher driving voltage and lower efficiency. The heterocyclic compound of the present application has a small steric hindrance in the polarization axis direction and a strong conjugation ability, and its performance in molecular film formation and charge transport is more excellent, so that the charge transport in the element is more balanced, and the performance of the element is significantly improved.

[0179] Although the present application has been described in detail with general description and specific embodiments above, some modifications or improvements can be made on the basis of the present application, which is obvious to those skilled in the art. Therefore, these modifications or improvements made on the basis of not deviating from the spirit of the present application, all belong to the scope of the present application claimed.

Claims

1. A heterocyclic compound, characterized by, The structural formula is shown as follows: ； wherein X 1 is CR 6 ; and 1 ; G is selected from O or S; R 1 selected from hydrogen; Ar 1 , Ar 2 each independently is selected from the group consisting of phenyl, naphthyl, anthryl, benzanthryl, phenanthryl, pyrenyl, chrysenyl, pyromethyl, tetracenyl, naphthacenyl, benzopyrenyl, biphenyl, terphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, dihydropyrenyl, triphenylenyl, dihydrotetraphenyl, tetrahydrophenyl, cis- or trans-indenofluorenyl, cis- or trans-indenocarbazolyl, indolocarbazolyl, benzofuranocarbazolyl, benzothienocarbazolyl, benzocarbazolyl, diphenylcarbazolyl, truxenyl, isotruxenyl, spirotruxenyl, spiroisotruxenyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, indolyl, isoindolyl, carbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo[5,6]quinolyl, benzo[6,7]quinolyl, benzo[7,8]quinolyl, phenoxazinyl, phenoxazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthimidazolyl, phenanthroimidazolyl, pyridimidazolyl, pyrazimidazolyl, quinoximidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthroxazolyl, phenanthroxazolyl, isoxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, hexaazatriphenylene, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazanthryl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazapyrenyl, pyrazinyl, phenoxazinyl, phenoxazinyl, phenothiazinyl, fluorubinyl, naphthidinyl, azacarbazolyl, benzocarbolinyl, carbolinyl, phenanthrolinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetrazinyl, 1,2,3,4-tetrazinyl, 1,2,3,5-tetrazinyl, purinyl, pteridinyl, indolizinyl, quinazolinyl, or benzothiadiazole; said L 1 , L 2 each independently is selected from the group consisting of a single bond or a group represented by 、 ； The dotted line represents the connection site of the group.

2. A heterocyclic compound, characterized by, The heterocyclic compound is selected from the compounds shown as follows: wherein T is selected from O, S, CMe2, CPh2, or NPh; X is selected from O or S; Me represents methyl, and Ph represents phenyl.

3. Use of the heterocyclic compound according to any one of claims 1 or 2 in the production of an organic electroluminescent element.

4. An organic electroluminescent element characterized by comprising the compound according to claim 1. It comprises: a first electrode, a second electrode, a capping layer, and one or more organic layers disposed between the first electrode and the second electrode; the material of at least one of the organic layers comprises the heterocyclic compound according to any one of claims 1 or 2.

5. The organic electroluminescent element according to claim 4, wherein The organic layer comprises a hole injection layer, a hole transport layer, a hole blocking layer, a light-emitting layer, an electron transport layer, an electron injection layer, or an electron blocking layer; the light-emitting layer, the electron transport layer, or the hole blocking layer comprises the heterocyclic compound according to any one of claims 1 or 2.

6. A consumer product characterized in that, It comprises the organic electroluminescent element according to claim 4.

Images