An organic electroluminescent device
By using specific triarylamine compounds and heterocyclic compounds in the luminescent layer of organic electroluminescent devices, the problems of low efficiency and short life are solved, and higher luminescence efficiency and longer service life are achieved.
Patent Information
- Application Number
- CN202310015463.4
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Filing Date
- 2023-01-05
- Publication Date
- 2025-06-24
- Estimated Expiration
- 2043-01-05
AI Technical Summary
Existing organic electroluminescent devices have low efficiency and short lifespan, and improvements in the luminescent layer materials are needed to improve performance.
Using a light emitting layer containing a specific triarylamine compound and a heterocyclic compound, the exciton utilization and the film stability of the light emitting layer are improved by adjusting the transport balance of holes and electrons.
Improves the luminous efficiency and service life of organic electroluminescent devices.
Smart Images

Figure BDA0004039913440000011 
Figure BDA0004039913440000021 
Figure BDA0004039913440000022
Abstract
Description
Technical Field
[0001] The present invention relates to the technical field of organic electroluminescence, and particularly to an organic electroluminescent device. Background Art
[0002] OLED, that is, organic light-emitting diode (Organic Light-Emitting Device), compared with the traditional liquid crystal display LCD (Liquid Crystal Display), the OLED display is not only ultra-light and ultra-thin, but also has the advantages of being bendable, high brightness, large viewing angle, fast response speed, self-luminous, and does not require a backlight. From mobile phones to TVs, almost all current display fields can become the target markets of OLEDs. Theoretically, it has a very bright and broad market prospect, so it has attracted strong research interest.
[0003] As early as the 1960s, Pope et al. first reported the electroluminescence phenomenon of anthracene single crystals, opening the prelude to the research on organic light-emitting devices. At present, a large number of research institutions and enterprises across the country have invested in the research, development and production of OLEDs. With the in-depth research, researchers have proposed a variety of OLED device structures to improve device performance. According to the number of organic layers in the device, OLED devices can be simply divided into single-layer devices, double-layer devices, triple-layer devices, multi-layer devices, etc. Among them, a typical organic electroluminescent device is a "sandwich" structure composed of a cathode, an electron transport layer (ETL, Electron Transport Layer), an emission layer (EML, Emission layer), a hole transport layer (HTL, Hole Transport Layer) and an anode. The anode mostly uses indium tin oxide (ITO), and the cathode usually uses a low work function metal. Under the action of an external electric field, the holes generated by the anode and the electrons generated by the cathode migrate to the emission layer. After reaching the emission layer, they recombine to generate excitons and release energy. The excitons migrate under the action of the electric field, transfer the energy to the luminescent material, and the electrons in the luminescent material molecules jump from the ground state to the excited state. Since the excited state is unstable, when the excitons return to the ground state in a radiative manner, a luminescence phenomenon occurs, which is called electroluminescence. After that, with the continuous improvement of technology, multi-layer structures have gradually developed, adding various functional auxiliary structures such as an electron injection layer, an electron blocking layer, a hole injection layer, and a hole blocking layer. These functional layers play different roles in the device.
[0004] In recent years, organic electroluminescent devices have made great progress in performance. However, there are still many problems in commercial production and application. Currently, the main problems of organic electroluminescent devices are low efficiency and short lifespan of the devices. Generally, a mixed system of a host material / dopant can be used as the light-emitting layer to improve the performance of the device. However, the selection of the host material is crucial, which has a great impact on the efficiency, lifespan, etc. of the device. Therefore, further in-depth research is needed to obtain organic electroluminescent devices with improved performance. Summary of the Invention
[0005] In view of the problems existing in the prior art, the present invention provides an organic electroluminescent device.
[0006] The present invention provides an organic electroluminescent device, comprising an anode, an organic layer, and a cathode. The organic layer is located between the anode and the cathode. The organic layer includes a light-emitting layer. The light-emitting layer contains a first host material and a second host material. The first host material is a triarylamine compound represented by Formula 1, and the second host material is a heterocyclic compound represented by Formula 2.
[0007]
[0008] Wherein, Ar1 and Ar2 are independently selected from one of the following groups:
[0009]
[0010] a0 is selected from an integer of 0 to 5; a1 is selected from an integer of 0 to 4; R1 is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic fused ring group, or two adjacent R1s are bonded to each other to form a substituted or unsubstituted ring; when there are more than two R1s, each R1 is the same or different from each other.
[0011] La, Lb, Lc, L1, and L2 are independently selected from one of a single bond, substituted or unsubstituted arylene, and substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic sub-fused ring group; and -La-Lb-Lc- is not a single bond.
[0012] The a is selected from integers from 0 to 4; the R is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C20 cycloaliphatic and C6-C30 aromatic fused ring group, or two adjacent Rs are bonded to each other to form a substituted or unsubstituted ring; when a is 2 or more, each R is the same as or different from each other;
[0013]
[0014] Wherein, the Ar is selected from one of the following groups
[0015]
[0016] The R0s are the same as or different from each other and are selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 cycloaliphatic and C6-C30 aromatic fused ring group, substituted or unsubstituted C3-C20 cycloaliphatic and C2-C30 heteroaromatic fused ring group, substituted or unsubstituted C3-C20 alicyclic heterocyclic group, or two adjacent R0s are bonded to each other to form a substituted or unsubstituted ring;
[0017] The X is selected from one of O, S, C(R x )2, N(R x ) and Si(R x )2, and the R x s are the same as or different from each other and are selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 cycloaliphatic and C6-C30 aromatic fused ring group, substituted or unsubstituted C3-C20 cycloaliphatic and C2-C30 heteroaromatic fused ring group, substituted or unsubstituted C3-C20 alicyclic heterocyclic group, or two adjacent R x s are bonded to each other to form a substituted or unsubstituted ring;
[0018] b0 is selected from integers from 0 to 4; b is selected from integers from 0 to 3; R5 is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 fused cycloalkyl and C6-C30 aryl ring group, substituted or unsubstituted C3-C20 fused cycloalkyl and C2-C30 heteroaryl ring group, substituted or unsubstituted C3-C20 heteroalicyclic group, or two adjacent R5 are bonded to each other to form a substituted or unsubstituted ring; when there are two or more R5, each R5 is the same or different from each other;
[0019] L0 is selected from a single bond or one of the following groups; n is selected from integers from 0 to 3; when n is 2 or more, each L0 is the same or different from each other;
[0020]
[0021] n1 is selected from integers from 0 to 4; R6 is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 fused cycloalkyl and C6-C30 aryl ring group, substituted or unsubstituted C3-C20 fused cycloalkyl and C2-C30 heteroaryl ring group, substituted or unsubstituted C3-C20 heteroalicyclic group, or two adjacent R6 are bonded to each other to form a substituted or unsubstituted ring; when n1 is 2 or more, each R6 is the same or different from each other;
[0022] L3 and L4 are independently selected from a single bond, substituted or unsubstituted C3-C20 sub-cycloalkyl, substituted or unsubstituted C6-C30 sub-aryl, substituted or unsubstituted C2-C30 sub-heteroaryl, substituted or unsubstituted C3-C20 fused cycloalkyl and C6-C30 aryl sub-fused ring group, substituted or unsubstituted C3-C20 fused cycloalkyl and C2-C30 sub-heteroaryl fused ring group;
[0023] R3 and R4 are independently selected from the following groups,
[0024]
[0025] R7 is selected from the group consisting of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 fused cycloaliphatic and C6-C30 aromatic ring groups, substituted or unsubstituted C3-C20 fused cycloaliphatic and C2-C30 heteroaromatic ring groups, and substituted or unsubstituted C3-C20 alicyclic heterocyclic groups;
[0026] X1 is selected from the group consisting of O, S, N(R x1 ), and R x1 is selected from the group consisting of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 fused cycloaliphatic and C6-C30 aromatic ring groups, substituted or unsubstituted C3-C20 fused cycloaliphatic and C2-C30 heteroaromatic ring groups, and substituted or unsubstituted C3-C20 alicyclic heterocyclic groups;
[0027] Y is the same or different and is selected from C(R y ), or N, and R y is selected from the group consisting of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 fused cycloaliphatic and C6-C30 aromatic ring groups, substituted or unsubstituted C3-C20 fused cycloaliphatic and C2-C30 heteroaromatic ring groups, and substituted or unsubstituted C3-C20 alicyclic heterocyclic groups, or two adjacent R y are bonded to each other to form a substituted or unsubstituted ring.
[0028] Advantageous effects: In the organic electroluminescent device of the present invention, since the light-emitting layer contains the first host material with hole characteristics shown in Formula 1 and the second host material with electron characteristics shown in Formula 2, the device can effectively adjust the transport balance of holes and electrons, and holes and electrons can recombine more effectively in the light-emitting layer to form excitons for light emission, the utilization rate of excitons is increased, and the formed light-emitting layer film is more stable. Therefore, the device containing the host material combination in the light-emitting layer of the present invention exhibits higher luminous efficiency and longer service life. Detailed embodiments
[0029] The present invention will be further illustrated below in conjunction with specific embodiments. It should be understood that these embodiments are only used to illustrate the present invention and not to limit the scope of the present invention. After reading the present invention, various equivalent modifications made by those skilled in the art fall within the scope claimed in this application.
[0030] In the present invention, "CXX-CYY of the substituted or unsubstituted ZZ group" means the number of carbon atoms in the "ZZ group" without substitution. When the "ZZ group" has a substituent, it does not include the carbon atoms of the substituent. For example, in "substituted or unsubstituted C1-C20 alkyl", "C1-C20" means the number of carbon atoms in the "alkyl" without substitution. When the "alkyl" has a substituent, it does not include the carbon atoms of the substituent. In "substituted or unsubstituted C6-C30 aryl", "C6-C30" means the number of carbon atoms in the "aryl" without substitution. When the "aryl" has a substituent, it does not include the carbon atoms in the substituent. In "substituted or unsubstituted C3-C20 cycloaliphatic and C6-C30 aromatic fused ring group", "C3-C20" means the number of carbon atoms in the "cycloaliphatic" without substitution. When the "cycloaliphatic" has a substituent, it does not include the carbon atoms of the substituent; "C6-C30" means the number of carbon atoms in the "aromatic ring" without substitution. When the "aromatic ring" has a substituent, it does not include the carbon atoms of the substituent. And so on.
[0031] In the present invention, "unsubstituted ZZ group" in "substituted or unsubstituted ZZ group" means that the hydrogen atoms of the "ZZ group" are not replaced by substituents. For example, in "substituted or unsubstituted C6-C30 aryl", "unsubstituted aryl" means that the hydrogen atoms of the "aryl" are not replaced by substituents. And so on.
[0032] In the present invention, "H", "hydrogen", and "hydrogen atom" include any isotope or isotope mixture, such as atoms with natural isotope abundances, as well as isotopes with different numbers of neutrons, including protium, deuterium, and tritium.
[0033] "Substituted or unsubstituted" as used in the present invention means that at least one hydrogen atom on a group is replaced by a substituent. When multiple hydrogens are replaced by multiple substituents, the multiple substituents may be the same or different. The position of the hydrogen replaced by the substituent can be any position. The substituents represented by "substituted" in the above "substituted or unsubstituted" include the following groups: deuterium, tritium, cyano, halogen, nitro, alkoxy, aryloxy, silyl, heterocyclic group, alkyl, cycloalkyl, aryl, heteroaryl, fused ring group of alicyclic and aromatic rings, fused ring group of alicyclic and heteroaromatic rings, arylamino, etc. In addition, each of the substituents can be substituted or unsubstituted. Two adjacent substituents can be bonded to form a ring. Preferred groups are as follows: deuterium, tritium, cyano, halogen, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, camphenyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, anthryl, pyrenyl, group, fluoranthenyl, fluorenyl, benzo[b]fluorenyl, spirobifluorenyl, spiroanthracenofluorenyl, benzocyclopropyl, benzocyclobutyl, indanyl, tetrahydronaphthyl, indenyl, dihydronaphthyl, carbazolyl, benzocarbazolyl, dibenzofuranyl, benzo[dibenzofuran]yl, dibenzothiophenyl, benzo[dibenzothiophene]yl, spirofluoreneoxanthenyl, spirofluoreneanthracenyl, spirofluorenenaphthalenyl, oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, imidazolyl, benzimidazolyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, etc.
[0034] The halogen described in the present invention includes fluorine, chlorine, bromine, and iodine.
[0035] The indane includes 2,3 - indane, and the tetrahydronaphthalene includes 1,2,3,4 - tetrahydronaphthalene.
[0036] In the present invention, if there are no special requirements, the substitution site on any group appearing in the present invention is any position on the group. For example, the substitution site of the group "tetrahydronaphthyl" can be either on the benzene ring or on the saturated six - membered ring.
[0037] In this specification, when the position of the substituent on the aromatic ring is not fixed, it means that it can be connected to any one of the corresponding optional sites of the aromatic ring. For example, can represent and so on.
[0038] In this specification, when the bond where the substituent or the connection site is located passes through two or more rings, it indicates that it can be connected to any one of the two or more rings, and specifically can be connected to any one of the corresponding optional sites of the ring. For example, can represent can represent And so on.
[0039] In the present invention, "adjacent two groups are bonded to form a ring" means that adjacent groups combine with each other and optionally aromatize to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring. The hydrocarbon ring can be an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring. The heterocyclic ring can include an aliphatic heterocyclic ring or an aromatic heterocyclic ring. The aliphatic hydrocarbon ring can be a saturated aliphatic hydrocarbon ring or an unsaturated aliphatic hydrocarbon ring, and the aliphatic heterocyclic ring can be a saturated aliphatic heterocyclic ring or an unsaturated aliphatic heterocyclic ring. The hydrocarbon ring and the heterocyclic ring can be monocyclic or polycyclic groups. In addition, the ring formed by the combination of adjacent groups can be connected to another ring to form a spiro structure. Examples are as follows:
[0040]
[0041] In the present invention, the ring formed by connection can be a five-membered ring, a six-membered ring or a fused ring, such as benzene, naphthalene, phenanthrene, triphenylene, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclobutene, cyclopentene, cyclohexene, cycloheptene, fluorene, pyridine, pyrimidine, dibenzofuran, dibenzothiophene, but not limited thereto. Among them, the alicyclic ring in "adjacent two groups are bonded to form an alicyclic ring" can be, for example, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclobutene, cyclopentene, cyclohexene, cycloheptene, etc., but not limited thereto.
[0042] The "integer selected from 0 to M" as described in the present invention means that the value is any one of the integers selected from 0 to M, including 0, 1, 2... M-2, M-1, M. For example, the "a0 is selected from the integers from 0 to 5" as described in the present invention means that a0 is selected from 0, 1, 2, 3, 4 or 5. The "a1 is selected from the integers from 0 to 4" means that a1 is selected from 0, 1, 2, 3 or 4. And so on.
[0043] The alkyl group as described in the present invention refers to a monovalent group formed by removing one hydrogen atom from an alkane molecule. The alkyl group can be a straight-chain alkyl group or a branched-chain alkyl group. The number of carbon atoms of the alkyl group is C1-C20, preferably C1-C15, more preferably C1-C10, and even more preferably C1-C6. Examples of the alkyl group include but are not limited to the following groups, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, etc. When the number of carbon atoms of the chain-like alkyl group described in the present invention is three or more, its isomers are included. For example, propyl includes n-propyl and isopropyl; butyl includes n-butyl, isobutyl, sec-butyl, tert-butyl. And so on.
[0044] The cycloalkyl group described in the present invention refers to a monovalent group formed by removing one hydrogen atom from a cycloalkane molecule. The number of carbon atoms in the cycloalkyl group is C3 - C20, preferably C3 - C15, more preferably C3 - C10. Examples of the cycloalkyl group include, but are not limited to, the groups described below, such as adamantyl, norbornyl, camphenyl, isocamphenyl, fenchyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, etc.
[0045] The aryl group described in the present invention refers to a monovalent group formed by removing one hydrogen atom from a carbon atom of an aromatic hydrocarbon molecule. The aryl group includes monocyclic aryl, polycyclic aryl, fused-ring aryl or a combination thereof. The number of carbon atoms in the aryl group is C6 - C60, preferably C6 - C30, preferably C6 - C25, more preferably C6 - C18, and even more preferably C6 - C12. Examples of the aryl group include, but are not limited to, the groups described below, such as phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthryl, triphenylenyl, anthryl, pyrenyl, fluoranthenyl, benzo[a]fluoranthenyl, -yl, fluorenyl, benzo[a]fluorenyl, dibenzo[a,h]fluorenyl, naphtho[2,1-a]fluorenyl, spirobifluorenyl, spiroanthracenofluorenyl, etc.
[0046] The heteroaryl group described in the present invention refers to a monovalent group in which at least one carbon atom in the aryl group is replaced by a heteroatom. The heteroatom is selected from O, S, N, Si, B, P, etc., but is not limited thereto. The number of carbon atoms in the heteroaryl group is C2 - C60, preferably C2 - C30, more preferably C2 - C25, and even more preferably C3 - C18. Examples of the heteroaryl group include, but are not limited to, the groups described below, such as furyl, benzofuryl, dibenzofuryl, benzo[d,e,f]triphenylene-2-yl, naphtho[2,1-a]dibenzofuran-4-yl, thienyl, benzothienyl, dibenzothienyl, benzo[d,e,f]triphenylene-4-yl, naphtho[2,1-a]dibenzothiophene-4-yl, carbazolyl, benzocarbazolyl, naphthocarbazolyl, dibenzocarbazolyl, spirofluorene-9,9'-xanthenyl, spirofluorene-9,9'-thioxanthenyl, spirofluorene-9,9'-acridinyl, oxazolyl, benzoxazolyl, naphthoxazolyl, phenanthro[4,5-bc]oxazolyl, anthra[2,3-b]oxazolyl, triphenylene[2,3-b]oxazolyl, thiazolyl, benzothiazolyl, naphthothiazolyl, phenanthro[4,5-bc]thiazolyl, anthra[2,3-b]thiazolyl, triphenylene[2,3-b]thiazolyl, imidazolyl, benzimidazolyl, naphthimidazolyl, phenanthro[4,5-bc]imidazolyl, anthra[2,3-b]imidazolyl, triphenylene[2,3-b]imidazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, phenanthroline, benzoquinolinyl, benzoisoquinolinyl, acridinyl, etc.
[0047] The alicyclics described in the present invention include cycloalkyl, cycloalkenyl, cycloalkynyl, etc. Examples of the alicyclic group include, but are not limited to, the following groups: cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, cyclopropene, cyclobutene, cyclopentene, cyclohexene, cycloheptene, etc. The number of carbon atoms of the alicyclic is C3-C25, preferably C3-C20, more preferably C3-C15, and still more preferably C3-C10.
[0048] The fused ring group of the alicyclic and aromatic ring described in the present invention refers to the general name of the monovalent group remaining after removing one hydrogen atom when the alicyclic and aromatic ring are fused together. The number of carbon atoms of the alicyclic is C3-C20, preferably C3-C15, more preferably C3-C10. The number of carbon atoms of the aromatic ring is C6-C30, preferably C6-C25, more preferably C6-C18, and still more preferably C6-C12. Examples of the fused ring group of the alicyclic and aromatic ring include, but are not limited to, the following groups: benzocyclopropyl, benzocyclobutyl, indanyl, tetrahydronaphthyl, benzocycloheptyl, indenyl, dihydronaphthyl, benzocycloheptenyl, naphthocyclopropyl, naphthocyclobutyl, naphthocyclopentyl, naphthocyclohexyl, etc.
[0049] The fused ring group of the alicyclic and heteroaromatic ring described in the present invention refers to the general name of the monovalent group remaining after removing one hydrogen atom when the alicyclic and heteroaromatic ring are fused together. The number of carbon atoms of the alicyclic is C3-C20, preferably C3-C15, more preferably C3-C10. The number of carbon atoms of the heteroaromatic ring is C2-C30, preferably C2-C25, more preferably C2-C18, and still more preferably C2-C12. Examples of the fused ring group of the alicyclic and aromatic ring include, but are not limited to, the following groups: pyridinocyclopropyl, pyridinocyclobutyl, pyridinocyclopentyl, pyridinocyclohexyl, pyridinobenzocycloheptyl, pyrimidinocyclopropyl, pyrimidinocyclobutyl, pyrimidinocyclopentyl, pyrimidinocyclohexyl, pyrimidinobenzocycloheptyl, dibenzofurancyclopentyl, dibenzofurancyclohexyl, dibenzofurancycloheptyl, dibenzothiophencyclopentyl, dibenzothiophencyclohexyl, dibenzothiophencycloheptyl, carbazolcyclopentyl, carbazolcyclohexyl, carbazolcycloheptyl, etc., but are not limited thereto.
[0050] The heterocyclic group refers to a monovalent group formed by removing one hydrogen atom from a carbon atom of a heterocyclic compound. The heteroatom is selected from O, S, N, Si, B, P, etc., but is not limited thereto. The heterocyclic group includes an aliphatic heterocyclic group and an aromatic heterocyclic group. The number of carbon atoms in the heterocyclic group is C2-C20, preferably C2-C15, more preferably C2-C10. Examples of the heterocyclic group include, but are not limited to, the following groups: azetidinyl, pyrrolidinyl, piperidinyl, azepanyl, morpholinyl, thiomorpholinyl, tetrahydrofuryl, tetrahydrothienyl, dioxane, furyl, dibenzofuryl, thienyl, dibenzothienyl, carbazolyl, benzocarbazolyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, etc.
[0051] The aliphatic heterocyclic group as used in the present invention refers to a divalent group formed by removing one hydrogen atom from an aliphatic heterocyclic hydrocarbon molecule. The heteroatom is selected from O, S, N, Si, B, P, etc., but is not limited thereto. The number of carbon atoms in the aliphatic heterocyclic group is C2-C20, preferably C2-C15, more preferably C2-C10. Examples of the aliphatic heterocyclic group include, but are not limited to, the following groups: azetidinyl, pyrrolidinyl, piperidinyl, azepanyl, homopiperidinyl, morpholinyl, thiomorpholinyl, tetrahydrofuryl, tetrahydrothienyl, dioxane, etc.
[0052] The arylene group as used in the present invention refers to a divalent group formed by removing two hydrogen atoms from a carbon atom in an aromatic hydrocarbon molecule. The arylene group includes a monocyclic arylene group, a polycyclic arylene group, a fused-ring arylene group or a combination thereof. The number of carbon atoms in the arylene group is C6-C60, preferably C6-C30, more preferably C6-C25, still more preferably C6-C18, and even more preferably C6-C12. Examples of the arylene group include, but are not limited to, the following groups: phenylene, biphenylene, terphenylenyl, quaterphenylene, naphthylene, phenanthrylene, triphenylene, anthrylene, pyrenylene, fluorenylene, benzofluorenylene, dibenzofluorenylene, naphthofluorenylene, spirobifluorenylene, benzospirobifluorenylene, spiroanthrylfluorenylene, etc.
[0053] The heteroarylene group refers to a divalent group in which at least one carbon atom in the arylene group is replaced by a heteroatom. The heteroatom is selected from O, S, N, Si, B, P, etc., but is not limited thereto. The number of carbon atoms in the heteroarylene group is C2-C60, preferably C2-C30, more preferably C2-C25, still more preferably C2-C12, and even more preferably C2-C7. The heteroarylene group includes monocyclic heteroarylene, polycyclic heteroarylene, fused heteroarylene or a combination thereof. Examples of the heteroarylene group include, but are not limited to, the following groups: dibenzofurandiyl, benzodibenzofurandiyl, dibenzothiophenediyl, benzodibenzothiophenediyl, carbazolediyl, benzocarbazolediyl, spirofluoreneanthradienediyl, spirofluoreneanthrathionediyl, spirofluoreneanthrazinediyl, benzoxazolediyl, naphthoxazolediyl, benzothiazolediyl, naphthothiazolediyl, imidazolediyl, pyridinediyl, pyrimidinediyl, pyrazinediyl, pyridazinediyl, triazinediyl, quinolinediyl, isoquinolinediyl, quinazolinediyl, quinoxalinediyl, naphthyridinediyl, phenanthrolinediyl, benzquinolinediyl, benzoisoquinolinediyl, etc.
[0054] The sub-fused ring group of the alicyclic and aromatic rings in the present invention refers to the general name of the divalent group remaining after removing two hydrogen atoms after the alicyclic ring and the aromatic ring are fused together. The number of carbon atoms in the alicyclic ring is C3-C20, preferably C3-C15, more preferably C3-C10. The number of carbon atoms in the aromatic ring is C6-C30, preferably C6-C25, more preferably C6-C18, and even more preferably C6-C12. Examples of the sub-fused ring group of the alicyclic and aromatic rings include, but are not limited to, the following groups: benzocyclopropylidene, benzocyclobutylidene, indanyl, tetrahydronaphthyl, benzocycloheptylidene, indenyl, dihydronaphthyl, benzocycloheptenylidene, naphthocyclopropylidene, naphthocyclobutylidene, naphthocyclopentylidene, naphthocyclohexylidene, etc., but are not limited thereto.
[0055] The sub-fused ring group of the alicyclic and heteroaromatic rings in the present invention refers to the general name of the divalent group remaining after removing two hydrogen atoms after the alicyclic ring and the heteroaromatic ring are fused together. The number of carbon atoms in the alicyclic ring is C3-C20, preferably C3-C15, more preferably C3-C10. The number of carbon atoms in the heteroaromatic ring is C2-C30, preferably C2-C25, more preferably C2-C18, and even more preferably C2-C12. Examples of the sub-fused ring group of the alicyclic and aromatic rings include, but are not limited to, the following groups: pyridinocyclopropylidene, pyridinocyclobutylidene, pyridinocyclopentylidene, pyridinocyclohexylidene, pyridinobenzocycloheptylidene, pyrimidinocyclobutylidene, pyrimidinocyclopentylidene, pyrimidinocyclohexylidene, etc., but are not limited thereto.
[0056] The present invention provides an organic electroluminescent device, comprising an anode, an organic layer, and a cathode. The organic layer is located between the anode and the cathode. The organic layer includes a light-emitting layer, and the light-emitting layer contains a first host material and a second host material. The first host material is a triarylamine compound represented by Formula 1, and the second host material is a heterocyclic compound represented by Formula 2.
[0057]
[0058] Wherein, Ar1 and Ar2 are independently selected from one of the groups shown below.
[0059]
[0060] a0 is selected from integers of 0 to 5; a1 is selected from integers of 0 to 4; R1 is selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic fused ring group, or two adjacent R1s are bonded to each other to form a substituted or unsubstituted ring; when there are more than two R1s, each R1 is the same or different from each other.
[0061] La, Lb, Lc, L1, and L2 are independently selected from a single bond, substituted or unsubstituted arylene, and substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic sub-fused ring group; and -La-Lb-Lc- is not a single bond.
[0062] a is selected from integers of 0 to 4; R is selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic fused ring group, or two adjacent Rs are bonded to each other to form a substituted or unsubstituted ring; when a is 2 or more, each R is the same or different from each other.
[0063]
[0064] Wherein, Ar is selected from one of the groups shown below.
[0065]
[0066] The R0s are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 fused cycloalkyl and C6-C30 aryl ring groups, substituted or unsubstituted C3-C20 fused cycloalkyl and C2-C30 heteroaryl ring groups, substituted or unsubstituted C3-C20 alicyclic heterocyclic groups, or two adjacent R0s are bonded to each other to form a substituted or unsubstituted ring;
[0067] The X is selected from the group consisting of O, S, C(R x )2, N(R x ) and Si(R x )2, and the R x s are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 fused cycloalkyl and C6-C30 aryl ring groups, substituted or unsubstituted C3-C20 fused cycloalkyl and C2-C30 heteroaryl ring groups, substituted or unsubstituted C3-C20 alicyclic heterocyclic groups, or two adjacent R x s are bonded to each other to form a substituted or unsubstituted ring;
[0068] The b0 is an integer from 0 to 4; the b is an integer from 0 to 3; the R5 is selected from the group consisting of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 fused cycloalkyl and C6-C30 aryl ring groups, substituted or unsubstituted C3-C20 fused cycloalkyl and C2-C30 heteroaryl ring groups, substituted or unsubstituted C3-C20 alicyclic heterocyclic groups, or two adjacent R5s are bonded to each other to form a substituted or unsubstituted ring; when there are two or more R5s, each R5 is the same or different from each other;
[0069] The L0 is selected from a single bond or one of the following groups; the n is an integer from 0 to 3; when n is 2 or more, each L0 is the same or different from each other;
[0070]
[0071] Said n1 is selected from integers from 0 to 4; said R6 is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 fused cycloaliphatic and C6-C30 aromatic ring groups, substituted or unsubstituted C3-C20 fused cycloaliphatic and C2-C30 heteroaromatic ring groups, substituted or unsubstituted C3-C20 alicyclic heterocyclic groups, or two adjacent R6 are bonded to each other to form a substituted or unsubstituted ring; when n1 is 2 or more, each R6 is the same or different from each other;
[0072] Said L3 and L4 are independently selected from one of a single bond, substituted or unsubstituted C3-C20 cycloalkylene, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C20 fused cycloaliphatic and C6-C30 aromatic ring groups, substituted or unsubstituted C3-C20 fused cycloaliphatic and C2-C30 heteroaromatic ring groups;
[0073] Said R3 and R4 are independently selected from the groups shown below,
[0074]
[0075] Said R7 is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 fused cycloaliphatic and C6-C30 aromatic ring groups, substituted or unsubstituted C3-C20 fused cycloaliphatic and C2-C30 heteroaromatic ring groups, substituted or unsubstituted C3-C20 alicyclic heterocyclic groups;
[0076] Said X1 is selected from one of O, S, N(R x1 ), said R x1 is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 fused cycloaliphatic and C6-C30 aromatic ring groups, substituted or unsubstituted C3-C20 fused cycloaliphatic and C2-C30 heteroaromatic ring groups, substituted or unsubstituted C3-C20 alicyclic heterocyclic groups;
[0077] Said Y is the same or different and is selected from C(R y) or N, said R y is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 fused cycloaliphatic and C6-C30 aromatic ring groups, substituted or unsubstituted C3-C20 fused cycloaliphatic and C2-C30 heteroaromatic ring groups, substituted or unsubstituted C3-C20 heteroalicyclic groups, or two adjacent Rs y are bonded to each other to form a substituted or unsubstituted ring.
[0078] Preferably, Ar1 and Ar2 are independently selected from one of the groups shown below,
[0079]
[0080] a0 is selected from integers from 0 to 5; a1 is selected from integers from 0 to 4; a2 is selected from integers from 0 to 7; a3 is selected from integers from 0 to 9;
[0081] R1 is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C20 fused cycloaliphatic and C6-C30 aromatic ring groups, or two adjacent R1s are bonded to each other to form a substituted or unsubstituted ring; when there are more than two R1s, each R1 is the same as or different from each other;
[0082] said R 10 is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C20 fused cycloaliphatic and C6-C30 aromatic ring groups, or two adjacent Rs 10 are bonded to each other to form a substituted or unsubstituted ring; when there are more than two Rs 10 each R 10 is the same as or different from each other;
[0083] Ra are the same as or different from each other and are selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C20 fused cycloaliphatic and C6-C30 aromatic ring groups, or two adjacent Ras are bonded to each other to form a substituted or unsubstituted ring; when there are more than two Ras, each Ra is the same as or different from each other.
[0084] Preferably, Ar1 and Ar2 are independently selected from one of the groups shown below.
[0085]
[0086] a0 is an integer selected from 0 to 5; a1 is an integer selected from 0 to 4; a2 is an integer selected from 0 to 7; a3 is an integer selected from 0 to 9; a4 is an integer selected from 0 to 6; a5 is an integer selected from 0 to 8; a6 is an integer selected from 0 to 10; a7 is an integer selected from 0 to 3; a8 is an integer selected from 0 to 12;
[0087] R1 is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C3-C15 alicyclic and C6-C25 aromatic fused ring group, or two adjacent R1s are bonded to each other to form a substituted or unsubstituted ring; when there are more than two R1s, each R1 is the same or different from each other;
[0088] R8 is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C3-C15 alicyclic and C6-C25 aromatic fused ring group; when there are more than two R8s, each R8 is the same or different from each other;
[0089] R 10 is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C3-C15 alicyclic and C6-C25 aromatic fused ring group, or two adjacent Rs 10 are bonded to each other to form a substituted or unsubstituted ring; when there are more than two Rs 10 exist, each R 10 is the same or different from each other.
[0090] Preferably, R1 is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C10 alicyclic and C6-C20 aromatic fused ring group, or two adjacent R1s are bonded to each other to form a substituted or unsubstituted alicyclic ring; when there are more than two R1s, each R1 is the same or different from each other.
[0091] Preferably, each of Ar1 and Ar2 independently is selected from one of the groups shown below:
[0092]
[0093]
[0094] a0 is selected from integers from 0 to 5; a1 is selected from integers from 0 to 4; a2 is selected from integers from 0 to 7; a3 is selected from integers from 0 to 9; a4 is selected from integers from 0 to 6; a5 is selected from integers from 0 to 8; a6 is selected from integers from 0 to 10; a7 is selected from integers from 0 to 3; a8 is selected from integers from 0 to 12; a9 is selected from integers from 0 to 2;
[0095] R1 is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C3-C10 cycloaliphatic and C6-C20 aromatic fused ring groups; when there are more than two R1s, each R1 is the same as or different from each other;
[0096] R8 is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C3-C10 cycloaliphatic and C6-C20 aromatic fused ring groups; when there are more than two R8s, each R8 is the same as or different from each other;
[0097] The R 10 is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C3-C10 cycloaliphatic and C6-C20 aromatic fused ring groups, or two adjacent Rs 10 are bonded to each other to form a substituted or unsubstituted ring; when there are more than two Rs 10 each R 10 is the same as or different from each other.
[0098] The R 11 is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C3-C10 cycloaliphatic and C6-C20 aromatic fused ring groups, or two adjacent Rs 11Bond with each other to form a substituted or unsubstituted ring; when there are more than two Rs 11 each R 11 is the same as or different from each other.
[0099] Preferably, the La, Lb, Lc, L1, L2 are independently selected from a single bond or one of the following groups; and the -La-Lb-Lc- is not a single bond;
[0100]
[0101] The m1 is selected from the integers of 0 to 4; the m2 is selected from the integers of 0 to 6; the m3 is selected from the integers of 0 to 5; the m4 is selected from the integers of 0 to 8; the m5 is selected from the integers of 0 to 3;
[0102] The R2 is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C20 cycloaliphatic and C6-C30 aromatic fused ring group, or two adjacent R2s bond with each other to form a substituted or unsubstituted ring; when there are more than two R2s, each R2 is the same as or different from each other;
[0103] The R 20 is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C20 cycloaliphatic and C6-C30 aromatic fused ring group, or two adjacent Rs 20 bond with each other to form a substituted or unsubstituted ring; when there are more than two Rs 20 each R 20 is the same as or different from each other;
[0104] The R m are the same as or different from each other and are selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C20 cycloaliphatic and C6-C30 aromatic fused ring group, or two adjacent Rs m bond with each other to form a substituted or unsubstituted ring;
[0105] The R m0 are the same as or different from each other and are selected from one of a single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C20 cycloaliphatic and C6-C30 aromatic sub-fused ring group.
[0106] Preferably, R2 is selected from the group consisting of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C3-C15 cycloaliphatic and C6-C25 aromatic fused ring group, or two adjacent R2 groups are bonded to each other to form a substituted or unsubstituted cycloaliphatic ring; when there are more than two R2 groups, each R2 group is the same as or different from each other.
[0107] Preferably, R is selected from the group consisting of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C3-C15 cycloaliphatic and C6-C25 aromatic fused ring group, or two adjacent R groups are bonded to each other to form a substituted or unsubstituted ring; when a is 2 or more, each R group is the same as or different from each other.
[0108] Preferably, R is selected from the group consisting of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted benzocyclopropyl, substituted or unsubstituted benzocyclobutyl, substituted or unsubstituted indanyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted indenyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptenyl, or two adjacent R groups are bonded to each other to form a substituted or unsubstituted ring; when a is 2 or more, each R group is the same as or different from each other; the substituents in the "substituted or unsubstituted" are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, benzocyclopropyl, benzocyclobutyl, indanyl, tetrahydronaphthyl, benzocycloheptyl, benzocyclobutenyl, indenyl, dihydronaphthyl.
[0109] Preferably, Ar is selected from one of the following groups
[0110]
[0111] b0 is selected from integers from 0 to 4; b is selected from integers from 0 to 3; b1 is selected from integers from 0 to 5; b2 is selected from integers from 0 to 6; b3 is selected from integers from 0 to 8; b4 is selected from integers from 0 to 10; b5 is selected from integers from 0 to 12;
[0112] R5 is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C15 cycloaliphatic and C6-C25 aromatic ring fused ring group, substituted or unsubstituted C3-C15 cycloaliphatic and C2-C25 heteroaromatic ring fused ring group, substituted or unsubstituted C3-C15 heteroalicyclic group, or two adjacent R5s are bonded to each other to form a substituted or unsubstituted ring; when there are two or more R5s, each R5 is the same as or different from each other;
[0113] R9 is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C15 cycloaliphatic and C6-C25 aromatic ring fused ring group, substituted or unsubstituted C3-C15 cycloaliphatic and C2-C25 heteroaromatic ring fused ring group, substituted or unsubstituted C3-C15 heteroalicyclic group; when there are two or more R9s, each R9 is the same as or different from each other;
[0114] R x are the same as or different from each other and are selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C15 cycloaliphatic and C6-C25 aromatic ring fused ring group, substituted or unsubstituted C3-C15 cycloaliphatic and C2-C25 heteroaromatic ring fused ring group, substituted or unsubstituted C3-C15 heteroalicyclic group, or two adjacent R x are bonded to each other to form a substituted or unsubstituted ring.
[0115] Preferably, L0 is selected from a single bond or one of the following groups; n is selected from integers from 0 to 3; when n is 2 or more, each L0 is the same as or different from each other;
[0116]
[0117] Said n1 is selected from integers from 0 to 4; said n2 is selected from integers from 0 to 6;
[0118] Said R6 is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 fused cycloalkyl of alicyclic ring and C6-C30 aryl ring, substituted or unsubstituted C3-C20 fused cycloalkyl of alicyclic ring and C2-C30 heteroaryl ring, substituted or unsubstituted C3-C20 alicyclic heterocyclic group, or two adjacent R6 are bonded to each other to form a substituted or unsubstituted ring; when there are more than two R6, each R6 is the same as or different from each other.
[0119] Preferably, said -(L0)n- is selected from a single bond or one of the following groups,
[0120]
[0121] Said n1 is selected from integers from 0 to 4; said n2 is selected from integers from 0 to 6;
[0122] Said R6 is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C15 fused cycloalkyl of alicyclic ring and C6-C25 aryl ring, substituted or unsubstituted C3-C15 fused cycloalkyl of alicyclic ring and C2-C25 heteroaryl ring, substituted or unsubstituted C3-C15 alicyclic heterocyclic group, or two adjacent R6 are bonded to each other to form a substituted or unsubstituted alicyclic ring; when there are more than two R6, each R6 is the same as or different from each other.
[0123] Preferably, said L3 and L4 are independently selected from a single bond or one of the following groups,
[0124]
[0125] Said Z are the same as or different from each other and are selected from C(R z ) or N, said R zOne selected from the same or different groups of hydrogen, deuterium, tritium, cyano group, halogen, nitro group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C3-C20 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted fused ring group of C3-C20 alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted fused ring group of C3-C20 alicyclic ring and C2-C30 heteroaromatic ring, substituted or unsubstituted C3-C20 alicyclic heterocyclic group, or two adjacent Rs z Bond with each other to form a substituted or unsubstituted ring.
[0126] Preferably, L3 and L4 are independently selected from a single bond or one of the following groups:
[0127]
[0128]
[0129] k1 is selected from integers of 0 to 4; k2 is selected from integers of 0 to 6; k3 is selected from integers of 0 to 3; k4 is selected from integers of 0 to 2; k5 is selected from integers of 0 to 5;
[0130] The R z One selected from the same or different groups of hydrogen, deuterium, tritium, cyano group, halogen, nitro group, substituted or unsubstituted C1-C15 alkyl group, substituted or unsubstituted C3-C15 cycloalkyl group, substituted or unsubstituted C6-C25 aryl group, substituted or unsubstituted C2-C25 heteroaryl group, substituted or unsubstituted fused ring group of C3-C15 alicyclic ring and C6-C25 aromatic ring, substituted or unsubstituted fused ring group of C3-C15 alicyclic ring and C2-C25 heteroaromatic ring, substituted or unsubstituted C3-C15 alicyclic heterocyclic group, or two adjacent Rs z Bond with each other to form a substituted or unsubstituted alicyclic ring.
[0131] Preferably, R3 and R4 are independently selected from one of the following groups:
[0132]
[0133] R7 is selected from one of hydrogen, deuterium, tritium, cyano group, halogen, nitro group, substituted or unsubstituted C1-C15 alkyl group, substituted or unsubstituted C3-C15 cycloalkyl group, substituted or unsubstituted C6-C25 aryl group, substituted or unsubstituted C2-C25 heteroaryl group, substituted or unsubstituted fused ring group of C3-C15 alicyclic ring and C6-C25 aromatic ring, substituted or unsubstituted fused ring group of C3-C15 alicyclic ring and C2-C25 heteroaromatic ring, substituted or unsubstituted C3-C15 alicyclic heterocyclic group;
[0134] The said R x1 is selected from one of hydrogen, deuterium, tritium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted fused ring group of C3-C15 alicyclic and C6-C25 aromatic ring, substituted or unsubstituted fused ring group of C3-C15 alicyclic and C2-C25 heteroaromatic ring, substituted or unsubstituted C3-C15 alicyclic heterocyclic group;
[0135] The said c1 is selected from integers from 0 to 4; the said c2 is selected from integers from 0 to 3; the said c3 is selected from integers from 0 to 2; the said R y is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted fused ring group of C3-C20 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted fused ring group of C3-C20 alicyclic and C2-C30 heteroaromatic ring, substituted or unsubstituted C3-C20 alicyclic heterocyclic group, or two adjacent Rs y bond to each other to form a substituted or unsubstituted ring; when there are more than two Rs y each R y are the same as or different from each other.
[0136] Preferably, the said R3 and R4 are independently selected from one of the groups shown below,
[0137]
[0138] The said R7 is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C2-C20 heteroaryl, substituted or unsubstituted fused ring group of C3-C10 alicyclic and C6-C20 aromatic ring, substituted or unsubstituted fused ring group of C3-C10 alicyclic and C2-C20 heteroaromatic ring, substituted or unsubstituted C3-C10 alicyclic heterocyclic group;
[0139] The said R x1Selected from one of hydrogen, deuterium, tritium, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C2-C20 heteroaryl, substituted or unsubstituted fused ring group of C3-C10 alicyclic and C6-C20 aromatic ring, substituted or unsubstituted fused ring group of C3-C10 alicyclic and C2-C20 heteroaromatic ring, substituted or unsubstituted C3-C10 alicyclic heterocyclic group;
[0140] The c1 is selected from integers from 0 to 4; the c2 is selected from integers from 0 to 3; the c3 is selected from integers from 0 to 2; the c4 is selected from integers from 0 to 6; the c5 is selected from integers from 0 to 8;
[0141] The R y is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted fused ring group of C3-C15 alicyclic and C6-C25 aromatic ring, substituted or unsubstituted fused ring group of C3-C15 alicyclic and C2-C25 heteroaromatic ring, substituted or unsubstituted C3-C15 alicyclic heterocyclic group, or two adjacent Rs y are bonded to each other to form a substituted or unsubstituted alicyclic ring; when there are more than two Rs y each R y is the same as or different from each other.
[0142] Preferably, the triarylamine compound represented by Formula 1 is selected from at least one of the following structures
[0143]
[0144]
[0145]
[0146]
[0147]
[0148]
[0149]
[0150]
[0151]
[0152]
[0153]
[0154]
[0155]
[0156]
[0157]
[0158]
[0159]
[0160]
[0161]
[0162]
[0163]
[0164]
[0165]
[0166]
[0167]
[0168] The above lists some specific chemical structures of the triarylamine compound shown in Formula 1 of the present invention. However, the present invention is not limited to these listed chemical structures. Any structure based on the structure shown in Formula 1 with substituents as defined above should be included.
[0169] Preferably, the heterocyclic compound shown in Formula 2 is selected from at least one of the following structures:
[0170]
[0171]
[0172]
[0173]
[0174]
[0175]
[0176]
[0177]
[0178]
[0179]
[0180]
[0181]
[0182]
[0183]
[0184]
[0185]
[0186]
[0187]
[0188]
[0189]
[0190]
[0191]
[0192]
[0193]
[0194]
[0195] The above lists some specific chemical structures of the heterocyclic compounds shown in Formula 2 of the present invention. However, the present invention is not limited to these listed chemical structures, and all those based on the structure shown in Formula 2 with substituents as defined above should be included.
[0196] Preferably, the light-emitting layer further contains a dopant.
[0197] The functional layers of the organic electroluminescent device of the present invention may further contain one or more of the following functional layers, such as a hole transport region, an electron transport region, and a cover layer. Any functional layer having hole injection and / or transport properties, electron injection and / or transport properties, or light extraction properties should be included. The hole transport region described in the present invention contains at least one of a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, an electron blocking layer, etc. The electron transport region described in the present invention contains at least one of a hole blocking layer, an electron transport layer, an electron injection layer, etc. Generally, the hole transport region and the electron transport region are located between the anode and the cathode, and the cover layer is located outside the cathode or the anode. Each functional layer may be composed of a single-layer thin film or a multi-layer thin film, and each thin film layer may be composed of only one material or multiple materials.
[0198] The present invention does not particularly limit the materials of the thin film layers in the organic electroluminescent device, and substances known in the art can be used. The following separately introduces the above-mentioned organic functional layers of the organic electroluminescent device and the electrodes on both sides of the device:
[0199] The function of the anode of the present invention is to smoothly inject holes into the organic layer, and the anode is composed of a material with a relatively high work function. The anode includes but is not limited to the following materials, metals or their alloys, metal oxides, combinations of metals and oxides, laminated materials, conductive polymers, etc. Specific examples may include gold (Au), chromium (Cr), copper (Cu), vanadium (V), aluminum (Al), indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide:aluminum (ZnO:Al), indium tin oxide / silver / indium tin oxide (ITO / Ag / ITO), polypyrrole, etc., but are not limited thereto.
[0200] The function of the cathode of the present invention is to smoothly inject electrons into the organic layer, and the cathode is composed of a material with a relatively low work function. The cathode includes but is not limited to the following materials, metals or their alloys, laminated materials, etc. Specific examples may include aluminum silver (Ag), aluminum (Al), tin (Sn), lead (Pb), magnesium / silver (Mg / Ag), lithium fluoride / aluminum (LiF / Al), lithium oxide / aluminum (Li2O / Al), etc., but are not limited thereto.
[0201] The function of the hole injection layer of the present invention is to reduce the interfacial barrier between the anode and the hole transport layer. The hole injection layer includes but is not limited to the materials described below, such as phthalocyanine metal complexes, polycyano conjugated organic compounds, annulene compounds, arylamine derivatives, polymers, etc. Specific examples may include copper phthalocyanine (CuPC), 4,4′-(1E,1′E)-(2-cyano-3,6-difluoro-5-isocyanocyclohex-2,5-diene-1,4-diylidene) bis(cyanomethan-1-ylidene) bis(2,3,5,6-tetrafluorobenzonitrile), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CN), 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyano-p-benzoquinodimethane (F4-TCNQ), 4,4'-bis[N-[9-(2-naphthyl)carbazol-3-yl]-N-phenylamino]-1,1'-biphenyl, 4,4',4”-tris(N-(1-naphthyl)-N-phenylamino)-triphenylamine (1-TNATA), 4,4',4”-tris(N,N-2-naphthylphenylamino)triphenylamine (2-TNATA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), etc., but not limited thereto.
[0202] The function of the hole transport layer of the present invention is to improve the balance of hole injection and transport in the device. The hole transport layer includes but is not limited to the materials described below, such as arylamine derivatives, carbazole derivatives, polymers, etc. Specific examples may include N,N'-diphenyl-N,N'-di(2-naphthyl)-1,1'-biphenyl-4,4'-diamine (β-NPB), N-([1,1'-biphenyl]-4-yl)-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-[1,1'-biphenyl]-4-amine, N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), 4,4',4”-tris(carbazol-9-yl)triphenylamine (TCTA), 1,3,5-tris(9-carbazolyl)benzene (TCB), poly(N-vinylcarbazole) (PVK), etc., but not limited thereto.
[0203] The function of the electron blocking layer of the present invention is to block electrons within the light-emitting layer, enabling effective recombination of electrons and holes within the light-emitting layer. The electron blocking layer includes but is not limited to the materials described below, such as arylamine derivatives, carbazole derivatives, etc. Specific examples may include N-phenylcarbazole, 4,4',4”-tris(N-carbazolyl)triphenylamine (TCTA), 4,4'-cyclohexylidenebis[N,N-bis(4-methylphenyl)aniline] (TAPC), N,N'-di(naphthalen-1-yl)-N,N'-diphenyl-benzidine (NPD), etc., but not limited thereto.
[0204] The light-emitting layer of the present invention comprises a host material and a dopant material. The light-emitting material can be a red light-emitting material, a green light-emitting material, a blue light-emitting material, or a combination thereof. The doping ratio of the host material and the dopant material can vary depending on the materials used. Generally, the doping ratio of the dopant material is 0.01% to 20%, preferably 0.1% to 15%, more preferably 1% to 10%.
[0205] The host material of the light-emitting layer not only needs to have bipolar charge transport properties but also requires appropriate energy levels to effectively transfer the excitation energy to the guest light-emitting material. The host material can be one material or two or more materials. Preferably, it is a triarylamine compound of Formula 1 of the present invention and a heterocyclic compound represented by Formula 2. The host material includes but is not limited to the following materials: heterocyclic compounds, metal complexes, fused aromatic ring derivatives, silicon-containing compounds, etc. Specific examples may include 9-[4-(tert-butyl)phenyl]-3,6-bis(triphenylmethyl)-9H-carbazole (CzC), 4,4'-bis(carbazol-9-yl)biphenyl (CBP), 4,4',4''-tris(N-carbazolyl)triphenylamine (TCTA), zinc 8-hydroxyquinolate (Znq2), tris(6-fluoro-8-hydroxyquinolinato)aluminum (6FAlq3), 9,10-di(2-naphthyl)anthracene (ADN), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (TBADN), 9,9-bis[4-(1-pyrenyl)phenyl]fluorene (DPPF), 2-[9,9-bis(4-methylphenyl)-fluoren-2-yl]-9,9-bis(4-methylphenyl)fluorene (BDAF), 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CzSi), etc., but are not limited thereto. The weight ratio of the first host material and the second host material of the present invention is 1:99 to 99:1, preferably 20:80 to 80:20, preferably 30:70 to 70:30, further preferably 40:60 to 60:40, more preferably 45:55 to 55:45, and most preferably 50:50.
[0206] The doping material can be a fluorescent material, a phosphorescent material, a TADF material, or a combination thereof. The doping material includes but is not limited to the materials described below, such as metal complexes, fused aromatic compounds, styrylamine compounds, aromatic amine derivatives, heterocyclic compounds, etc. Specific examples may include bis(3,5-difluoro-2-(2-pyridyl)phenyl-(2-carboxypyridyl)iridium(III) (FIrPic), tris(2-(3,5-dimethylphenyl)quinoline-C2,N')iridium(III) (Ir(dmpq)3), bis(2-(3,5-dimethylphenyl)quinoline-C2,N')(acetylacetonate)iridium(III) (Ir(mphq)2acac), bis(2-phenylpyridine)iridium(acetylacetonate) (Ir(ppy)2(acac)), tris[2-(p-tolyl)pyridine]iridium(III) (Ir(mppy)3), N 1 ,N 1 ,N 6 ,N 6 tetrakis([1,1'-biphenyl]-3-yl)pyrene-1,6-diamine, N 1 ,N 6 bis(6-(tert-butyl)dibenz[b,d]furan-4-yl)-N1,N6-di-m-tolyl-pyrene-1,6-diamine, 2,5,8,11-tetra-tert-butylperylene (TBPe), N,N,N',N'-tetrakis(4-methylphenyl)-[9,9'-bianthracene]-10,10'-diamine (BA-TTB), 4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl (DPAVBi), 4,4'-bis(4-(9H-carbazol-9-yl)styryl)biphenyl (BSB4), 2,8-di-tert-butyl-5,11-bis(4-tert-butylphenyl)-6,12-diphenyltetradecene (TBRb), 4-(dicyanovinyl)-2-tert-butyl-6-(1,1,7,7-tetramethyljulolidin-4-ylvinyl)-4H-pyran (DCJTB), coumarin 6, etc., but not limited thereto.
[0207] The function of the hole blocking layer of the present invention is to block holes within the light-emitting layer, enabling effective recombination of holes and electrons within the light-emitting layer. The hole blocking layer includes but is not limited to the materials described below, such as oxadiazole derivatives, triazole derivatives, imidazole derivatives, phenanthroline derivatives, metal complexes, etc. Specific examples may include 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), 1,3,5-tris(N-phenyl-2-benzimidazolyl)benzene (TPBi), 4,7-diphenyl-1,10-phenanthroline (Bphen), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), bis(2-methyl-8-hydroxyquinolinato-N1,O8)-(1,1'-biphenyl-4-olato)aluminum (BAlq), etc., but not limited thereto.
[0208] The function of the electron transport layer of the present invention is to improve the balance of electron injection and transport in the device. The electron transport layer includes but is not limited to the materials described below, such as metal complexes, heteroaromatic compounds, polymers, etc. Specific examples may include tris(8-quinolinolato)aluminum(III) (Alq3), 8-(4-(4,6-bis(naphthalen-2-yl)-1,3,5-triazin-2-yl)phenyl)quinoline, 1,3-bis[2-(2,2'-bipyridin-6-yl)-1,3,4-oxadiazol-5-yl]benzene (Bpy-OXD), 3,5-diphenyl-4-(1-naphthyl)-1,2,4-triazole (NTAZ), 2,9-(dimethyl)-4,7-diphenyl-1,10-phenanthroline (BCP), 3,3'-[5',5”-bis[3-(4-pyridyl)phenyl][1,1':3',1”:3”,1”'-quaterphenyl]-3,3”'-diyl]dipyridine (BP4mPy), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (PF-BPy), etc., but not limited thereto.
[0209] The function of the electron injection layer of the present invention is to reduce the interfacial barrier between the cathode and the electron transport layer. The electron injection layer materials include but are not limited to the materials described below, such as metals, metal compounds, metal oxides, etc. Specific examples may include lithium (Li), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), cesium carbonate (Cs2CO3), lithium oxide (Li2O), etc., but not limited thereto.
[0210] There is no particular limitation on the preparation method of each layer of thin film in the organic electroluminescent device of the present invention, and methods such as vacuum evaporation, sputtering, spin coating, spraying, screen printing, laser transfer printing, etc. can be used, but not limited thereto.
[0211] The organic electroluminescent device of the present invention is mainly applied in the field of information display technology and is widely used in various information displays in information display, such as tablet computers, flat panel TVs, mobile phones, smart watches, digital cameras, VR, vehicle-mounted systems, wearable devices, etc.
[0212] Synthesis Example
[0213] There is no particular limitation on the preparation method of the triarylamine compound shown in Structural Formula 1 of the present invention, and conventional methods well-known to those skilled in the art can be used. For example, carbon-nitrogen coupling reaction, carbon-carbon coupling reaction, etc. The triarylamine compound shown in Formula 1 of the present invention can be prepared by the following synthetic route.
[0214]
[0215] There is no particular limitation on the preparation method of the heterocyclic compound shown in Structural Formula 2 of the present invention, and conventional methods well-known to those skilled in the art can be adopted. For example, carbon-nitrogen coupling reaction, carbon-carbon coupling reaction, etc. The heterocyclic compound shown in Formula 2 of the present invention can be prepared by the following synthetic route.
[0216] (1) When R3-L3-* is the same as R4-L4-*, the synthetic route of Formula 2 is as follows:
[0217]
[0218] (2) When R3-L3-* is different from R4-L4-*, the synthetic route of Formula 2 is as follows:
[0219]
[0220] The Xn is a halogen, for example, Xn is independently selected from Cl, Br, I;
[0221] The Bn is independently selected from *-B(OH)2, etc.
[0222] Raw materials and reagents: The present invention has no particular limitation on the raw materials or reagents used in the following synthesis examples, and they can be commercially available products or prepared by methods well-known to those skilled in the art. The raw materials and reagents used in the present invention are all of reagent grade.
[0223] Instruments: G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer (Waters, UK); Vario ELcube type organic elemental analyzer (Elementar, Germany).
[0224] Synthesis Example 1
[0225]
[0226] Synthesis of A-12:
[0227] Under nitrogen protection, a-12 (120.00mmol, 20.07g), 1,10-phenanthroline (24.00mmol, 4.32g), anhydrous K3PO4 (240.00mmol, 50.94g), b-12 (120.00mmol, 22.97g), DMSO (350.00ml), CuI (24.00mmol, 4.57g) were added to the reaction bottle, heated and stirred, and refluxed for 24 hours. After the reaction was completed, the reaction solution was cooled to room temperature, quenched with water, and then extracted with chloroform. A small amount of activated carbon was added to the organic phase, heated under reflux for 0.5 hours for decolorization, filtered, and the solvent was removed under reduced pressure. Column chromatography was performed, and the mobile phase was dichloromethane: petroleum ether (1:5) to obtain A-12 (26.67g, 80%). The solid purity detected by HPLC was ≥99.81%.
[0228] Synthetic B-12:
[0229] Under nitrogen protection, A-12 (80.00mmol, 22.22g), c-12 (80.00mmol, 13.54g), sodium tert-butoxide (120.00mmol, 11.53g), toluene (250.00mL), palladium acetate (0.80mmol, 180mg), tri-tert-butylphosphine (1.20mmol, 243mg) were added to the reaction bottle, stirred and dissolved, and refluxed for 5 hours. After the reaction was completed, the reaction solution was cooled to room temperature, water was added, extracted with dichloromethane, the organic phase was dried with anhydrous magnesium sulfate, filtered, the solvent was removed under reduced pressure, and recrystallized with toluene: methanol = 8:1 to obtain B-12 (24.30g, yield 74%), and the solid purity was ≥99.84% by HPLC.
[0230] Synthesis 1-12:
[0231] Under nitrogen protection, add B-12 (40.00mmol, 16.42g), d-12 (40.00mmol, 8.52g), sodium tert-butoxide (80.00mmol, 7.69g), toluene (200.00mL), tridibenzylideneacetone dipalladium (0.40mmol, 366mg) and tri-tert-butylphosphine (0.80mmol, 162mg) to the reaction bottle, stir to dissolve, and reflux for 8 hours. After the reaction is completed, the reaction solution is cooled to room temperature, water is added, extracted with chloroform, the organic phase is dried with anhydrous magnesium sulfate, filtered, the solvent is removed under reduced pressure, and recrystallized from toluene to obtain compound 1-12 (17.15g, yield 79%). The solid purity detected by HPLC is ≥99.93%. Mass spectrum m / z: 542.2733 (theoretical value: 542.2722). Theoretical element content (%) C 40 H 34N2: C, 88.52; H, 6.31; N, 5.16. Measured elemental content (%): C, 88.56; H, 6.33; N, 5.13.
[0232] Synthesis Example 2
[0233]
[0234] According to the same preparation method as in 1-12 of Synthesis Example 1, replace a-12 with an equimolar amount of a-26, b-12 with an equimolar amount of b-135, and d-12 with an equimolar amount of d-135 to obtain 1-135 (24.97 g), and the solid purity detected by HPLC is ≥99.94%. Mass spectrometry m / z: 878.3651 (theoretical value: 878.3661). Theoretical elemental content (%) C 67 H 46 N2: C, 91.54; H, 5.27; N, 3.19. Measured elemental content (%): C, 91.51; H, 5.29; N, 3.18.
[0235] Synthesis Example 3
[0236]
[0237] According to the same preparation method as in 1-12 of Synthesis Example 1, replace a-12 with an equimolar amount of a-142, b-12 with an equimolar amount of b-142, and d-12 with an equimolar amount of d-142 to obtain 1-189 (20.21 g), and the solid purity detected by HPLC is ≥99.92%. Mass spectrometry m / z: 688.2647 (theoretical value: 688.2627). Theoretical elemental content (%) C 50 H 32 N4: C, 87.18; H, 4.68; N, 8.13. Measured elemental content (%): C, 87.21; H, 4.65; N, 8.15.
[0238] Synthesis Example 4
[0239]
[0240] According to the same preparation method as in 1-12 of Synthesis Example 1, replace b-12 with an equimolar amount of b-189 and d-12 with an equimolar amount of d-189 to obtain 1-189 (20.21 g), and the solid purity detected by HPLC is ≥99.94%. Mass spectrometry m / z: 664.3685 (theoretical value: 664.3694). Theoretical elemental content (%) C 49 H 32D8N2: C, 88.51; H, 7.27; N, 4.21. Measured elemental content (%): C, 88.55; H, 7.25; N, 4.19.
[0241] Synthesis Example 5
[0242]
[0243] According to the same preparation method as in 1-12 of Synthesis Example 1, replace a-12 with an equimolar amount of a-494, b-12 with an equimolar amount of b-494, c-12 with an equimolar amount of c-494, and d-12 with an equimolar amount of d-494 to obtain 1-494 (22.48 g), and the solid purity detected by HPLC is ≥99.95%. Mass spectrometry m / z: 769.3518 (theoretical value: 769.3505). Theoretical elemental content (%) C 58 H 35 D5N2: C, 90.47; H, 5.89; N, 3.64. Measured elemental content (%): C, 90.45; H, 5.86; N, 3.68.
[0244] Synthesis Example 6
[0245]
[0246] According to the same preparation method as in 1-12 of Synthesis Example 1, replace b-12 with an equimolar amount of b-524, c-12 with an equimolar amount of c-524, and d-12 with an equimolar amount of d-524 to obtain 1-524 (22.09 g), and the solid purity detected by HPLC is ≥99.89%. Mass spectrometry m / z: 788.3183 (theoretical value: 788.3191). Theoretical elemental content (%) C 60 H 40 N2: C, 91.34; H, 5.11; N, 3.55. Measured elemental content (%): C, 91.32; H, 5.16; N, 3.51.
[0247] Synthesis Example 7
[0248]
[0249] According to the same preparation method as in 1-12 of Synthesis Example 1, replace b-12 with an equimolar amount of b-539, c-12 with an equimolar amount of c-539, and d-12 with an equimolar amount of d-539 to obtain 1-539 (23.46 g), and the solid purity detected by HPLC is ≥99.91%. Mass spectrometry m / z: 781.3517 (theoretical value: 781.3505). Theoretical elemental content (%) C 59 H 35D5N2: C, 90.62; H, 5.80; N, 3.58. Measured elemental content (%): C, 90.59; H, 5.85; N, 3.56.
[0250] Synthesis Example 8: Preparation of Compound 2-5
[0251]
[0252] Preparation of Intermediate F-5:
[0253] Under nitrogen protection, successively add Intermediate e-5 (33.64 g, 110.00 mmol), raw material bis(pinacolato)diboron (30.73 g, 121.00 mmol), Pd(dppf)Cl2 (1.84 g, 2.51 mmol), KOAc (21.59 g, 220.00 mmol), and 1,4-dioxane (520 mL) to the reaction flask. Stir the mixture, heat the above reaction system to reflux for 4.5 hours. After the reaction is completed, cool to room temperature, add 780 mL of distilled water, then extract with ethyl acetate. The organic layer is dried with anhydrous MgSO4, the ethyl acetate is removed by rotary evaporation, and then recrystallized with toluene to obtain Intermediate F-5 (34.09 g, yield 78%); HPLC purity ≥ 98.66%.
[0254] Preparation of Intermediate G-5:
[0255] Under nitrogen protection, successively add Intermediate F-5 (28.38 g, 71.43 mmol), raw material g-5 (15.81 g, 70.00 mmol), Pd(dppf)Cl2 (0.77 g, 1.05 mmol), Na2CO3 (14.84 g, 140.00 mmol), 210 mL of toluene, 70 mL of ethanol, and 70 mL of water to the reaction flask. Stir the mixture, heat the above reaction system to reflux for 6 hours; after the reaction is completed, cool to room temperature, filter to obtain the filter cake, and wash the filter cake with ethanol. Finally, recrystallize the filter cake with toluene / methanol = 7:1 to obtain Intermediate G-5 (22.44 g, yield 77%); HPLC purity ≥ 98.71%.
[0256] Preparation of Intermediate H-5:
[0257] Under nitrogen protection, intermediate G-5 (18.74 g, 45.00 mmol), raw material bis(pinacolato)diboron (25.14 g, 99.00 mmol), Pd(dppf)Cl2 (1.98 g, 2.70 mmol), KOAc (17.67 g, 180.00 mmol), and 1,4-dioxane (450 mL) were successively added to a reaction flask. The mixture was stirred, and the above reaction system was heated to reflux for 7.5 hours. After the reaction was completed, it was cooled to room temperature, 700 mL of distilled water was added, and then it was extracted with ethyl acetate. The organic layer was dried over anhydrous MgSO4, the ethyl acetate was removed by rotary evaporation, and then it was recrystallized with toluene and dried to obtain intermediate H-5 (19.42 g, yield 72%); HPLC purity ≥ 98.89%.
[0258] Preparation of compound 2-5:
[0259] Under nitrogen protection, intermediate H-5 (17.98 g, 30.00 mmol), raw material h-5 (12.18 g, 61.50 mmol), Pd2(dba)3 (0.55 g, 0.60 mmol), P(t-Bu)3 (2.4 mL of 0.5 M toluene solution, 1.2 mmol), K2CO3 (120.00 mmol, 16.59 g), and 120 ml of tetrahydrofuran were successively added to a reaction flask. The mixture was stirred, and the above reaction system was heated to reflux for 8 hours. After the reaction was completed, it was cooled to room temperature, the filter cake was obtained by filtration, and the filter cake was rinsed with ethanol. Finally, the filter cake was recrystallized with toluene to obtain compound 2-5 (13.26 g, yield 76%); HPLC purity ≥ 99.83%. Mass spectrum m / z: 581.2112 (theoretical value: 581.2103). Theoretical elemental content (%) C 40 H 27 N3O2: C, 82.60; H, 4.68; N, 7.22. Measured elemental content (%): C, 82.63; H, 4.64; N, 7.24.
[0260] Synthesis example 9: Preparation of compound 2-19
[0261]
[0262] Preparation of intermediate E-19:
[0263] Under nitrogen protection, raw material e-19 (35.56 g, 110.00 mmol), raw material f-19 (17.54 g, 112.20 mmol), Pd(PPh3)4 (2.54 g, 2.20 mmol), K2CO3 (30.41 g, 220.00 mmol), 330 mL of toluene, 110 mL of ethanol, and 110 mL of water were successively added to the reaction flask. The mixture was stirred, and the above reaction system was heated to reflux for 3.5 hours. After the reaction was completed, it was cooled to room temperature, and the filter cake was obtained by suction filtration. The filter cake was rinsed with ethanol. Finally, the filter cake was recrystallized with toluene / methanol = 6:1 to obtain intermediate E-19 (32.40 g, yield 83%); HPLC purity ≥ 98.69%.
[0264] According to the same preparation method as that of compound 2-5 in Synthesis Example 1, equimolar amounts of e-5 and h-5 were respectively replaced with equimolar amounts of E-19 and h-19 to obtain compound 2-19 (17.38 g), HPLC purity ≧ 99.93%. Mass spectrometry m / z: 782.2945 (theoretical value: 782.2933). Theoretical elemental content (%) C 57 H 38 N2O2: C, 87.44; H, 4.89; N, 3.58. Measured elemental content (%): C, 87.42; H, 4.86; N, 3.60.
[0265] Synthesis Example 10: Preparation of Compound 2-28
[0266]
[0267] According to the same preparation method as that of compound 2-19 in Synthesis Example 9, equimolar amounts of e-19, f-19, and h-19 were respectively replaced with equimolar amounts of e-28, f-28, and h-28 to obtain compound 2-28 (13.77 g), HPLC purity ≧ 99.95%. Mass spectrometry m / z: 732.3731 (theoretical value: 732.3716). Theoretical elemental content (%) C 52 H 48 N2O2: C, 85.21; H, 6.60; N, 3.82. Measured elemental content (%): C, 85.18; H, 6.62; N, 3.80.
[0268] Synthesis Example 11: Preparation of Compound 2-47
[0269]
[0270] According to the same preparation method as that of Compound 2-19 in Synthesis Example 9, replace equimolar amounts of e-19, f-19, and h-19 with equimolar amounts of e-47, f-47, and h-5 respectively to obtain Compound 2-47 (17.32 g), with HPLC purity ≥ 99.94%. Mass spectrometry m / z: 790.3570 (theoretical value: 790.3559). Theoretical elemental content (%) C 57 H 46 N2O2: C, 86.55; H, 5.86; N, 3.54. Measured elemental content (%): C, 86.58; H, 5.82; N, 3.51.
[0271] Synthesis Example 12: Preparation of Compound 2-55
[0272]
[0273]
[0274] According to the same preparation method as that of Compound 2-19 in Synthesis Example 9, replace equimolar amounts of e-19, f-19, and h-19 with equimolar amounts of e-55, f-55, and h-5 respectively to obtain Compound 2-55 (13.78 g), with HPLC purity ≥ 99.95%. Mass spectrometry m / z: 656.2452 (theoretical value: 656.2464). Theoretical elemental content (%) C 47 H 32 N2O2: C, 85.95; H, 4.91; N, 4.27. Measured elemental content (%): C, 85.92; H, 4.93; N, 4.25.
[0275] Synthesis Example 13: Preparation of Compound 2-72
[0276]
[0277] According to the same preparation method as that of Compound 2-19 in Synthesis Example 9, replace equimolar amounts of e-19, f-19, and h-19 with equimolar amounts of e-72, f-72, and h-5 respectively to obtain Compound 2-72 (14.37 g), with HPLC purity ≥ 99.94%. Mass spectrometry m / z: 656.2451 (theoretical value: 656.2464). Theoretical elemental content (%) C 47 H 32 N2O2: C, 85.95; H, 4.91; N, 4.27. Measured elemental content (%): C, 85.98; H, 4.93; N, 4.23.
[0278] Synthesis Example 14: Preparation of Compound 2-79
[0279]
[0280] According to the same preparation method as that of Compound 2-19 in Synthesis Example 9, equimolar amounts of e-19, f-19, and g-5 were respectively replaced with equimolar amounts of e-79, f-72, and g-79 to obtain Compound 2-79 (18.44 g), with HPLC purity ≥ 99.95%. Mass spectrometry m / z: 808.3098 (theoretical value: 808.3090). Theoretical elemental content (%) C 59 H 40 N2O2: C, 87.60; H, 4.98; N, 3.46. Measured elemental content (%): C, 87.63; H, 4.97; N, 3.48.
[0281] Synthesis Example 15: Preparation of Compound 2-87
[0282]
[0283]
[0284] According to the same preparation method as that of Compound 2-19 in Synthesis Example 9, equimolar amounts of e-19 and f-19 were respectively replaced with equimolar amounts of e-87 and f-87 to obtain Compound 2-87 (18.36 g), with HPLC purity ≥ 99.92%. Mass spectrometry m / z: 815.3542 (theoretical value: 815.3529). Theoretical elemental content (%) C 59 H 33 D7N2O2: C, 86.84; H, 5.80; N, 3.43. Measured elemental content (%): C, 86.87; H, 5.78; N, 3.46.
[0285] Synthesis Example 16: Preparation of Compound 2-98
[0286]
[0287] According to the same preparation method as that of Compound 2-19 in Synthesis Example 9, equimolar amounts of e-19, f-19, and h-19 were respectively replaced with equimolar amounts of e-28, f-47, and h-98 to obtain Compound 2-98 (17.47 g), with HPLC purity ≥ 99.96%. Mass spectrometry m / z: 810.2981 (theoretical value: 810.2995). Theoretical elemental content (%) C 57 H 38 N4O2: C, 84.42; H, 4.72; N, 6.91. Measured elemental content (%): C, 84.46; H, 4.70; N, 6.88.
[0288] Synthesis Example 17: Preparation of Compound 2-99
[0289]
[0290] According to the same preparation method of Compound 2-19 in Synthesis Example 9, equimolar amounts of e-19, f-19, and h-19 were respectively replaced with equimolar amounts of e-28, f-47, and h-99 to obtain Compound 2-99 (17.01 g), with HPLC purity ≥ 99.91%. Mass spectrometry m / z: 812.2926 (theoretical value: 812.2900). Theoretical elemental content (%) C 55 H 36 N6O2: C, 81.26; H, 4.46; N, 10.34. Measured elemental content (%): C, 81.22; H, 4.44; N, 10.37.
[0291] Synthesis Example 18: Preparation of Compound 2-107
[0292]
[0293]
[0294] According to the same preparation method of Compound 2-19 in Synthesis Example 9, equimolar amounts of e-19, f-19, and h-19 were respectively replaced with equimolar amounts of e-28, f-107, and h-107 to obtain Compound 2-107 (18.49 g), with HPLC purity ≥ 99.94%. Mass spectrometry m / z: 810.2981 (theoretical value: 810.2995). Theoretical elemental content (%) C 57 H 38 N4O2: C, 84.42; H, 4.72; N, 6.91. Measured elemental content (%): C, 84.45; H, 4.70; N, 6.94.
[0295] Synthesis Example 19: Preparation of Compound 2-126
[0296]
[0297] According to the same preparation method of Compound 2-19 in Synthesis Example 9, equimolar amounts of e-19, f-19, and h-19 were respectively replaced with equimolar amounts of e-28, f-47, and h-126 to obtain Compound 2-126 (18.17 g), with HPLC purity ≥ 99.95%. Mass spectrometry m / z: 840.2641 (theoretical value: 840.2633). Theoretical elemental content (%) C 59 H 40 N2S2: C, 84.25; H, 4.79; N, 3.33. Measured elemental content (%): C, 84.28; H, 4.75; N, 3.35.
[0298] Synthesis Example 20: Preparation of Compound 2-138
[0299]
[0300] According to the same preparation method as that of Compound 2-19 in Synthesis Example 9, equimolar amounts of e-19, f-19, and h-19 were respectively replaced with equimolar amounts of e-28, f-138, and h-5 to obtain Compound 2-138 (16.27 g), with HPLC purity ≥ 99.93%. Mass spectrometry m / z: 732.2762 (theoretical value: 732.2777). Theoretical elemental content (%) C 53 H 36 N2O2: C, 86.86; H, 4.95; N, 3.82. Measured elemental content (%): C, 86.83; H, 4.97; N, 3.84.
[0301] Synthesis Example 21: Preparation of Compound 2-150
[0302]
[0303]
[0304] According to the same preparation method as that of Compound 2-19 in Synthesis Example 9, equimolar amounts of e-19, f-19, and h-19 were respectively replaced with equimolar amounts of e-28, f-150, and h-150 to obtain Compound 2-150 (16.52 g), with HPLC purity ≥ 99.91%. Mass spectrometry m / z: 764.2334 (theoretical value: 764.2320). Theoretical elemental content (%) C 53 H 36 N2S2: C, 83.21; H, 4.74; N, 3.66. Measured elemental content (%): C, 83.25; H, 4.72; N, 3.63.
[0305] Synthesis Example 22: Preparation of Compound 2-176
[0306]
[0307] According to the same preparation method as that of Compound 2-19 in Synthesis Example 9, equimolar amounts of e-19, f-19, and h-19 were respectively replaced with equimolar amounts of e-72, f-176, and h-176 to obtain Compound 2-176 (19.02 g), with HPLC purity ≥ 99.96%. Mass spectrometry m / z: 892.2682 (theoretical value: 892.2694). Theoretical elemental content (%) C 61 H 40N4S2: C, 82.03; H, 4.51; N, 6.27. Measured elemental content (%): C, 82.06; H, 4.53; N, 6.24.
[0308] Synthesis Example 23: Preparation of Compound 2-329
[0309]
[0310] According to the same preparation method as in Compound 2-19 of Synthesis Example 9, equimolar amounts of e-19, f-19, and h-19 were respectively replaced with equimolar amounts of e-329, f-329, and h-150 to obtain Compound 2-329 (18.13 g), with HPLC purity ≥ 99.92%. Mass spectrometry m / z: 862.2489 (theoretical value: 862.2476). Theoretical elemental content (%) C 61 H 38 N2S2: C, 84.89; H, 4.44; N, 3.25. Measured elemental content (%): C, 84.86; H, 4.42; N, 3.28.
[0311] Synthesis Example 24: Preparation of Compound 2-355
[0312]
[0313]
[0314] According to the same preparation method as in Compound 2-19 of Synthesis Example 9, equimolar amounts of e-19, f-19, and h-19 were respectively replaced with equimolar amounts of e-355, f-355, and h-355 to obtain Compound 2-355 (19.43 g), with HPLC purity ≥ 99.94%. Mass spectrometry m / z: 886.2465 (theoretical value: 886.2476). Theoretical elemental content (%) C 63 H 38 N2S2: C, 85.30; H, 4.32; N, 3.16. Measured elemental content (%): C, 85.33; H, 4.30; N, 3.18.
[0315] Synthesis Example 25: Preparation of Compound 2-432
[0316]
[0317] According to the same preparation method as in Compound 2-19 of Synthesis Example 9, equimolar amounts of e-19 were respectively replaced with equimolar amounts of e-432 to obtain Compound 2-432 (19.08 g), with HPLC purity ≥ 99.96%. Mass spectrometry m / z: 856.3097 (theoretical value: 856.3090). Theoretical elemental content (%) C 63H 40 N2O2: C, 88.29; H, 4.70; N, 3.27. Measured elemental content (%): C, 88.25; H, 4.73; N, 3.23.
[0318] Synthesis Example 26: Preparation of Compound 2-446
[0319]
[0320] According to the same preparation method of Compound 2-19 in Synthesis Example 9, equimolar amounts of e-19, f-19, and h-19 were respectively replaced with equimolar amounts of e-446, f-47, and h-150 to obtain Compound 2-446 (18.05 g), with HPLC purity ≥ 99.97%. Mass spectrometry m / z: 812.2311 (theoretical value: 812.2320). Theoretical elemental content (%) C 57 H 36 N2S2: C, 84.20; H, 4.46; N, 3.45. Measured elemental content (%): C, 84.23; H, 4.42; N, 3.42.
[0321] Synthesis Example 27: Preparation of Compound 2-478
[0322]
[0323]
[0324] According to the same preparation method of Compound 2-19 in Synthesis Example 9, equimolar amounts of e-19, f-19, and h-19 were respectively replaced with equimolar amounts of e-478, f-47, and h-5 to obtain Compound 2-478 (16.18 g), with HPLC purity ≥ 99.95%. Mass spectrometry m / z: 748.3099 (theoretical value: 748.3090). Theoretical elemental content (%) C 54 H 40 N2O2: C, 86.60; H, 5.38; N, 3.74. Measured elemental content (%): C, 86.64; H, 5.34; N, 3.77.
[0325] Synthesis Example 28: Preparation of Compound 2-512
[0326]
[0327] According to the same preparation method as that of Compound 2-19 in Synthesis Example 9, equimolar amounts of e-19, f-19, and h-19 were respectively replaced with equimolar amounts of e-512, f-47, and h-512 to obtain Compound 2-512 (19.23 g), with HPLC purity ≥ 99.94%. Mass spectrometry m / z: 928.2959 (theoretical value: 928.2946). Theoretical elemental content (%) C 66 H 44 N2S2: C, 85.31; H, 4.77; N, 3.01. Measured elemental content (%): C, 85.34; H, 4.75; N, 3.03.
[0328] Device Example
[0329] In the present invention, the ITO / Ag / ITO or ITO glass substrate was ultrasonically cleaned twice with 5% glass cleaning solution for 20 minutes each time, and then ultrasonically cleaned twice with deionized water for 10 minutes each time. It was ultrasonically cleaned with acetone and isopropanol in sequence for 20 minutes and dried at 120 °C. All organic materials were sublimated with purity above 99.99%.
[0330] A combined IVL test system was composed of a test software, a computer, a K2400 digital source meter produced by Keithley Corporation in the United States, and a PR788 spectral scanning luminance meter of PhotoResearch Corporation in the United States to test the driving voltage, luminous efficiency, and CIE color coordinates of the organic electroluminescent device. The lifetime test was carried out using an M6000 OLED lifetime test system of McScience Corporation. The test environment was an atmospheric environment and the temperature was room temperature.
[0331] Example 1: Preparation of Organic Electroluminescent Device 1
[0332] 1-TNATA was vacuum-evaporated on the ITO anode as a hole injection layer with a thickness of 60 nm; β-NPB was vacuum-evaporated on the hole injection layer as a hole transport layer with a thickness of 41 nm; the first host compound 1-12 and the second host compound 2-226 were vacuum-evaporated on the hole transport layer at a mass ratio of 1:1, and the dopant Ir(mphq)2acac was evaporated at a doping amount of 4 wt% based on the total amount of the host and the dopant to form a light-emitting layer with a thickness of 50 nm; NBphen was vacuum-evaporated on the light-emitting layer as a hole blocking layer with a thickness of 6 nm; Alq3 was vacuum-evaporated on the hole blocking layer as an electron transport layer with a thickness of 22 nm; LiF was vacuum-evaporated on the electron transport layer as an electron injection layer with an evaporation thickness of 1.1 nm; Al was vacuum-evaporated on the electron injection layer as a cathode with a thickness of 160 nm.
[0333] Examples 2 to 35: Preparation of Organic Electroluminescent Devices 2 to 35
[0334] Replace the first host compound 1-12 in the light-emitting layer of Example 1 with compound 1-25, compound 1-32, compound 1-37, compound 1-61, compound 1-71, compound 1-81, compound 1-109, compound 1-127, compound 1-130, compound 1-149, compound 1-156, compound 1-175, compound 1-199, compound 1-204, compound 1-218, compound 1-220, compound 1-230, compound 1-249, compound 1-275, compound 1-280, compound 1-302, compound 1-309, compound 1-319, compound 1-320, compound 1-325, compound 1-370, compound 1-476, compound 1-585, compound 1-670, compound 1-701, compound 1-708, compound 1-758, compound 1-774, compound 1-815 respectively; replace the second host compound 2-226 in the light-emitting layer with compound 2-82, compound 2-446, compound 2-228, compound 2-8, compound 2-211, compound 2-5, compound 2-432, compound 2-21, compound 2-22, compound 2-28, compound 2-360, compound 2-150, compound 2-16, compound 2-18, compound 2-478, compound 2-79, compound 2-687, compound 2-13, compound 2-12, compound 2-83, compound 2-99, compound 2-158, compound 2-138, compound 2-64, compound 2-73, compound 2-250, compound 2-55, compound 2-19, compound 2-355, compound 2-705, compound 2-721, compound 2-329, compound 2-176, compound 2-33 respectively, and keep other steps the same to obtain organic electroluminescent devices 2 to 35.
[0335] Comparative Example 1: Preparation of the comparative organic electroluminescent device 1
[0336] 1-TNATA was vacuum-evaporated on the ITO anode as the hole injection layer with a thickness of 60 nm; β-NPB was vacuum-evaporated on the hole injection layer as the hole transport layer with a thickness of 41 nm; compound 1-12 was vacuum-evaporated on the hole transport layer, and the dopant Ir(mphq)2acac was evaporated with a doping amount of 4 wt% based on the total amount of the host and the dopant to form the light-emitting layer with a thickness of 50 nm; NBphen was vacuum-evaporated on the light-emitting layer as the hole blocking layer with a thickness of 6 nm; Alq3 was vacuum-evaporated on the hole blocking layer as the electron transport layer with a thickness of 22 nm; LiF was vacuum-evaporated on the electron transport layer as the electron injection layer with an evaporation thickness of 1.1 nm; Al was vacuum-evaporated on the electron injection layer as the cathode with a thickness of 160 nm.
[0337] Comparative Examples 2-12: Preparation of Organic Electroluminescent Devices 2-12
[0338] In Comparative Example 1, compound 1-12 in the light-emitting layer was replaced with compound 1-25, compound 1-81, compound 1-204, compound 1-585, compound 1-701, compound 2-5, compound 2-18, compound 2-19, compound 2-82, compound 2-226, and compound 2-705 respectively, and the other steps were the same, to obtain organic electroluminescent devices 2-12.
[0339]
[0340] The test results of the light-emitting characteristics of the organic electroluminescent devices prepared in Examples 1-35 and Comparative Examples 1-12 of the present invention are shown in Table 1.
[0341] Table 1 Test Data of the Light-Emitting Characteristics of Organic Electroluminescent Devices
[0342]
[0343]
[0344]
[0345] As can be seen from Table 1, the organic electroluminescent devices 1-35 of the present invention have higher luminous efficiency and longer service life compared with the comparative devices 1-12, and the performance of the devices has been significantly improved.
[0346] Example 36: Preparation of Organic Electroluminescent Device 36
[0347] HI-1 was vacuum-evaporated on the ITO anode as the first hole injection layer with a thickness of 65 nm; HAT-CN was vacuum-evaporated on the first hole injection layer as the second hole injection layer with a thickness of 4 nm; HT-1 was vacuum-evaporated on the second hole injection layer as the hole transport layer with a thickness of 40 nm; the first host compound 1-12 and the second host compound 2-234 were vacuum-evaporated on the hole transport layer at a mass ratio of 1:1, and the dopant Ir(ppy)2(acac) was evaporated at a doping amount of 9 wt% based on the total amount of the host and the dopant to form a light-emitting layer with a thickness of 46 nm; ET-1:Liq = 1:1 (wt%) was vacuum-evaporated on the light-emitting layer as the electron transport layer with a thickness of 28 nm; Liq was vacuum-evaporated on the electron transport layer as the electron injection layer with an evaporation thickness of 1.3 nm; Al was vacuum-evaporated on the electron injection layer as the cathode with a thickness of 110 nm.
[0348] Examples 37 to 70: Preparation of Organic Electroluminescent Devices 37 to 70
[0349] The first host compound 1-12 in the light-emitting layer of Example 36 was replaced with Compound 1-25, Compound 1-48, Compound 1-51, Compound 1-61, Compound 1-67, Compound 1-73, Compound 1-99, Compound 1-127, Compound 1-135, Compound 1-142, Compound 1-156, Compound 1-172, Compound 1-189, Compound 1-197, Compound 1-199, Compound 1-204, Compound 1-216, Compound 1-249, Compound 1-267, Compound 1-316, Compound 1-320, Compound 1-476, Compound 1-491, Compound 1-494, Compound 1-495, Compound 1-524, Compound 1-539, Compound 1-568, Compound 1-585, Compound 1-599, Compound 1-642, Compound 1-763, Compound 1-787, Compound 1-815 respectively;
[0350] The second host compound 1-234 was replaced with compound 2-99, compound 2-478, compound 2-687, compound 2-72, compound 2-26, compound 2-226, compound 2-19, compound 2-87, compound 2-11, compound 2-605, compound 2-63, compound 2-31, compound 2-138, compound 2-14, compound 2-47, compound 2-23, compound 2-107, compound 2-250, compound 2-75, compound 2-544, compound 2-64, compound 2-344, compound 2-79, compound 2-211, compound 2-329, compound 2-5, compound 2-616, compound 2-432, compound 2-158, compound 2-30, compound 2-126, compound 2-755, compound 2-41, compound 2-512 respectively, and the other steps were the same, to obtain organic electroluminescent devices 37 to 70.
[0351] Comparative Example 13: Preparation of Comparative Organic Electroluminescent Device 13
[0352] HI-1 was vacuum-evaporated on the ITO anode as the first hole injection layer with a thickness of 65 nm; HAT-CN was vacuum-evaporated on the first hole injection layer as the second hole injection layer with a thickness of 4 nm; HT-1 was vacuum-evaporated on the second hole injection layer as the hole transport layer with a thickness of 40 nm; compound 1-48 was vacuum-evaporated on the hole transport layer, and the dopant Ir(ppy)2(acac) was evaporated with a doping amount of 9 wt% based on the total amount of the host and the dopant to form a light-emitting layer with a thickness of 46 nm; ET-1:Liq = 1:1 (wt%) was vacuum-evaporated on the light-emitting layer as the electron transport layer with a thickness of 28 nm; Liq was vacuum-evaporated on the electron transport layer as the electron injection layer with an evaporation thickness of 1.3 nm; Al was vacuum-evaporated on the electron injection layer as the cathode with a thickness of 110 nm.
[0353] Comparative Examples 14 to 24: Preparation of Organic Electroluminescent Devices 14 to 24
[0354] Compound 1-48 in the light-emitting layer of Comparative Example 1 was replaced with compound 1-51, compound 1-73, compound 1-172, compound 1-267, compound 1-316, compound 2-31, compound 2-75, compound 2-226, compound 2-478, compound 2-544, compound 2-687 respectively, and the other steps were the same, to obtain comparative organic electroluminescent devices 14 to 24.
[0355]
[0356] The test results of the luminescence characteristics of the organic electroluminescent devices prepared in Examples 36 to 70 and Comparative Examples 13 to 24 of the present invention are shown in Table 2.
[0357] Table 2 Test data of the luminescence characteristics of the organic electroluminescent devices
[0358]
[0359]
[0360] As can be seen from Table 1, the organic electroluminescent devices 36 to 70 of the present invention have higher luminous efficiency and longer service life compared with the comparative devices 13 to 24, and the device performance has been significantly improved.
[0361] The light-emitting layer of the organic electroluminescent device of the present invention comprises a first host material having hole characteristics shown in Formula 1 and a second host material having electron characteristics shown in Formula 2. The device comprising the host material combination of the present invention in the light-emitting layer can effectively balance the injection and transport of holes and electrons, enable holes and electrons to effectively recombine to form excitons in the light-emitting layer, the utilization rate of excitons is relatively high, and the formed light-emitting layer film is more stable. Therefore, it can effectively improve the luminous efficiency of the device and significantly increase the service life of the organic electroluminescent device.
[0362] It should be noted that the present invention has been specifically described with individual embodiments. However, without departing from the principle of the present invention, those of ordinary skill in the art can make various improvements in forms or details to the present invention, and these improvements also fall within the protection scope of the present invention.
Claims
1. An organic electroluminescent device, comprising an anode, an organic layer, and a cathode, wherein the organic layer is located between the anode and the cathode, and the organic layer includes a light-emitting layer, characterized in that, The light-emitting layer contains a first host material and a second host material, and the weight ratio of the first host material to the second host material is 30:70 to 70:
30. The first host material is a triarylamine compound represented by Formula 1, and the second host material is a heterocyclic compound represented by Formula 2. Wherein, Ar1 and Ar2 are independently selected from one of the groups shown below. a0 is selected from integers from 0 to 5; a1 is selected from integers from 0 to 4; a2 is selected from integers from 0 to 7; a3 is selected from integers from 0 to 9; a4 is selected from integers from 0 to 6; a5 is selected from integers from 0 to 8; a6 is selected from integers from 0 to 10; a7 is selected from integers from 0 to 3; a8 is selected from integers from 0 to 12. Ra are the same or different and are each selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C18 aryl, "substituted or unsubstituted fused ring group of C3-C10 alicyclic ring and C6-C12 aromatic ring". When there are two or more Ra, each Ra is the same or different from each other. R1 is selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C18 aryl, "substituted or unsubstituted fused ring group of C3-C10 alicyclic ring and C6-C12 aromatic ring", or two adjacent R1 are bonded to each other to form a substituted or unsubstituted benzene ring, naphthalene ring, cyclopropane ring, cyclobutane ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, cyclobutene ring, cyclopentene ring, cyclohexene ring, cycloheptene ring. When there are two or more R1, each R1 is the same or different from each other. R8 is selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C18 aryl, "substituted or unsubstituted fused ring group of C3-C10 alicyclic ring and C6-C12 aromatic ring". When there are two or more R8, each R8 is the same or different from each other. The R 10 is selected from one of hydrogen, deuterium, tritium, cyano group, halogen, nitro group, substituted or unsubstituted C1-C10 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C6-C18 aryl group, "fused ring group of substituted or unsubstituted C3-C10 alicyclic ring and C6-C12 aromatic ring", or two adjacent Rs 10 are bonded to each other to form a substituted or unsubstituted: benzene ring, naphthalene ring, cyclopropane ring, cyclobutane ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, cyclobutene ring, cyclopentene ring, cyclohexene ring, cycloheptene ring; when there are more than two Rs 10 each R 10 is the same as or different from each other; La, Lb, Lc, L1, and L2 are independently selected from a single bond or one of the groups shown below; and -La-Lb-Lc- is not a single bond. m1 is selected from integers from 0 to 4; m2 is selected from integers from 0 to 6; m3 is selected from integers from 0 to 5; m4 is selected from integers from 0 to 8; m5 is selected from integers from 0 to 3. R2 is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C18 aryl, "substituted or unsubstituted fused ring group of C3-C10 alicyclic ring and C6-C12 aromatic ring", or two adjacent R2 are bonded to each other to form a substituted or unsubstituted: benzene ring, naphthalene ring, cyclopropane ring, cyclobutane ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, cyclobutene ring, cyclopentene ring, cyclohexene ring, cycloheptene ring; when there are more than two R2, each R2 is the same as or different from each other; The R 20 is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C18 aryl, "fused ring group of substituted or unsubstituted C3-C10 alicyclic ring and C6-C12 aromatic ring", or two adjacent Rs 20 are bonded to each other to form a substituted or unsubstituted: benzene ring, naphthalene ring, cyclopropane ring, cyclobutane ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, cyclobutene ring, cyclopentene ring, cyclohexene ring, cycloheptene ring; when there are more than two Rs 20 each R 20 is the same as or different from each other; The R m which is the same as or different from one selected from hydrogen, deuterium, tritium, cyano group, halogen, nitro group, substituted or unsubstituted C1-C10 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C6-C18 aryl group, "fused ring group of substituted or unsubstituted C3-C10 alicyclic ring and C6-C12 aromatic ring", or two adjacent Rs m are bonded to each other to form a substituted or unsubstituted: cyclopropane ring, cyclobutane ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, cyclobutene ring, cyclopentene ring, cyclohexene ring, cycloheptene ring; Said R m0 Same or different and selected from one of a single bond, a substituted or unsubstituted C6-C18 arylene group, and "a sub-fused ring group of a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring"; a is selected from an integer of 0-4; R is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C18 aryl, "substituted or unsubstituted fused ring group of C3-C12 alicyclic ring and C6-C12 aromatic ring", or two adjacent R are bonded to each other to form a substituted or unsubstituted: benzene ring, naphthalene ring, cyclopropane ring, cyclobutane ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, cyclobutene ring, cyclopentene ring, cyclohexene ring, cycloheptene, pyridine ring, pyrimidine ring; when a is 2 or more, each R is the same as or different from each other; wherein, Ar is selected from one of the following groups, R0 is the same as or different from each other and is selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C2-C18 heteroaryl, "substituted or unsubstituted fused ring group of C3-C10 alicyclic ring and C6-C12 aromatic ring", "substituted or unsubstituted fused ring group of C3-C10 alicyclic ring and C2-C12 heteroaromatic ring", substituted or unsubstituted C3-C10 alicyclic heterocyclic group; X is selected from one of O, S, C(R x )2, N(R x ), wherein each R x , which may be the same or different, is selected from hydrogen, deuterium, tritium, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C2-C18 heteroaryl, "fused ring group of a substituted or unsubstituted C3-C10 alicyclic ring and a C6-C12 aromatic ring", "fused ring group of a substituted or unsubstituted C3-C10 alicyclic ring and a C2-C12 heteroaromatic ring", substituted or unsubstituted C3-C10 alicyclic heterocyclic group, or two adjacent Rs x are bonded to each other to form a substituted or unsubstituted: cyclopropane ring, cyclobutane ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, cyclobutene ring, cyclopentene ring, cyclohexene ring, cycloheptene; b0 is selected from an integer of 0-4; b is selected from an integer of 0-3; b1 is selected from an integer of 0-5; b2 is selected from an integer of 0-6; b3 is selected from an integer of 0-8; b4 is selected from an integer of 0-10; b5 is selected from an integer of 0-12; R5 is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C2-C18 heteroaryl, "substituted or unsubstituted fused ring group of C3-C10 alicyclic ring and C6-C12 aromatic ring", "substituted or unsubstituted fused ring group of C3-C10 alicyclic ring and C2-C12 heteroaromatic ring", substituted or unsubstituted C3-C10 alicyclic heterocyclic group, or two adjacent R5s are bonded to each other to form a substituted or unsubstituted: benzene ring, naphthalene ring, cyclopropane ring, cyclobutane ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, cyclobutene ring, cyclopentene ring, cyclohexene ring, cycloheptene, pyridine ring, pyrimidine ring; when there are more than two R5s, each R5 is the same as or different from each other; R9 is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C2-C18 heteroaryl, "substituted or unsubstituted fused ring group of C3-C10 alicyclic ring and C6-C12 aromatic ring", "substituted or unsubstituted fused ring group of C3-C10 alicyclic ring and C2-C12 heteroaromatic ring", substituted or unsubstituted C3-C10 alicyclic heterocyclic group; when there are more than two R9s, each R9 is the same as or different from each other; L0 is selected from a single bond or one of the following groups; n is an integer from 0 to 3; when n is 2 or more, each L0 is the same as or different from each other; n1 is an integer from 0 to 4; n2 is an integer from 0 to 6; R6 is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C2-C18 heteroaryl, "substituted or unsubstituted fused ring group of C3-C10 alicyclic ring and C6-C12 aromatic ring", "substituted or unsubstituted fused ring group of C3-C10 alicyclic ring and C2-C12 heteroaromatic ring", substituted or unsubstituted C3-C10 alicyclic heterocyclic group, or two adjacent R6s are bonded to each other to form a substituted or unsubstituted: benzene ring, naphthalene ring, cyclopropane ring, cyclobutane ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, cyclobutene ring, cyclopentene ring, cyclohexene ring, cycloheptene, pyridine ring, pyrimidine ring; when there are more than two R6s, each R6 is the same as or different from each other; L3 and L4 are independently selected from a single bond or one of the following groups, The Z are the same or different and are selected from C(R z ), or N, and the R z are the same or different and are selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C2-C18 heteroaryl, "substituted or unsubstituted fused ring group of C3-C10 alicyclic ring and C6-C12 aromatic ring", "substituted or unsubstituted fused ring group of C3-C10 alicyclic ring and C2-C12 heteroaromatic ring", substituted or unsubstituted C3-C10 alicyclic heterocyclic group, or two adjacent R z are bonded to each other to form a substituted or unsubstituted: benzene ring, naphthalene ring, cyclopropane ring, cyclobutane ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, cyclobutene ring, cyclopentene ring, cyclohexene ring, cycloheptene ring, pyridine ring, pyrimidine ring; R3 and R4 are independently selected from the following groups, R7 is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C2-C18 heteroaryl, "fused ring group of substituted or unsubstituted C3-C10 alicyclic ring and C6-C12 aromatic ring", "fused ring group of substituted or unsubstituted C3-C10 alicyclic ring and C2-C12 heteroaromatic ring", and substituted or unsubstituted C3-C10 alicyclic heterocyclic group; X1 is selected from one of O, S, N(R x1 ), and R x1 is selected from one of hydrogen, deuterium, tritium, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C2-C18 heteroaryl, "fused ring group of substituted or unsubstituted C3-C10 alicyclic and C6-C12 aromatic ring", "fused ring group of substituted or unsubstituted C3-C10 alicyclic and C2-C12 heteroaromatic ring", substituted or unsubstituted C3-C10 alicyclic heterocyclic group; The Ys are the same or different and are each independently selected from C(R y ), or N, and the R y s are each independently selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C2-C18 heteroaryl, "substituted or unsubstituted fused ring group of a C3-C10 alicyclic ring and a C6-C12 aromatic ring", "substituted or unsubstituted fused ring group of a C3-C10 alicyclic ring and a C2-C12 heteroaromatic ring", substituted or unsubstituted C3-C10 alicyclic heterocyclic group, or two adjacent R y s are bonded to each other to form a substituted or unsubstituted: benzene ring, naphthalene ring, cyclopropane ring, cyclobutane ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, cyclobutene ring, cyclopentene ring, cyclohexene ring, cycloheptene ring, pyridine ring, pyrimidine ring; The substituents represented by "substituted" in the "substituted or unsubstituted" include the following groups: deuterium, tritium, cyano, halogen, nitro, methyl, ethyl, propyl, butyl, phenyl.
2. An organic electroluminescent device according to claim 1, wherein Ar1 and Ar2 are independently selected from one of the following groups: a0 is selected from integers of 0-5; a1 is selected from integers of 0-4; a2 is selected from integers of 0-7; a3 is selected from integers of 0-9; a4 is selected from integers of 0-6; a5 is selected from integers of 0-8; a6 is selected from integers of 0-10; a7 is selected from integers of 0-3; a8 is selected from integers of 0-12; R1 is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C12 aryl, or two adjacent R1s are bonded to each other to form a substituted or unsubstituted benzene ring, cyclopropane ring, cyclobutane ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, cyclobutene ring, cyclopentene ring, cyclohexene ring, cycloheptene ring; when there are more than two R1s, each R1 is the same or different from each other; R8 is selected from one of hydrogen, deuterium, tritium, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C12 aryl; when there are more than two R8s, each R8 is the same or different from each other; The R 10 is selected from one of hydrogen, deuterium, tritium, cyano group, halogen, nitro group, substituted or unsubstituted C1-C6 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C6-C12 aryl group, or two adjacent Rs 10 are bonded to each other to form a substituted or unsubstituted: benzene ring, cyclopropane ring, cyclobutane ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, cyclobutene ring, cyclopentene ring, cyclohexene ring, cycloheptene ring; when there are more than two Rs 10 each R 10 is the same as or different from each other.
3. An organic electroluminescent device according to claim 1, characterized in that, La, Lb, Lc, L1, L2 are independently selected from a single bond or one of the following groups; and -La-Lb-Lc- is not a single bond; R2 is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C12 aryl, or two adjacent R2s are bonded to each other to form a substituted or unsubstituted benzene ring, cyclopropane ring, cyclobutane ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, cyclobutene ring, cyclopentene ring, cyclohexene ring, cycloheptene ring; when there are more than two R2s, each R2 is the same or different from each other; The R 20 is selected from one of hydrogen, deuterium, tritium, cyano group, halogen, nitro group, substituted or unsubstituted C1-C6 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C6-C12 aryl group, or two adjacent Rs 20 are bonded to each other to form a substituted or unsubstituted: benzene ring, cyclopropane ring, cyclobutane ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, cyclobutene ring, cyclopentene ring, cyclohexene ring, cycloheptene ring; when there are more than two Rs 20 each R 20 is the same as or different from each other; The R m is the same as or different from one selected from hydrogen, deuterium, tritium, cyano group, halogen, nitro group, substituted or unsubstituted C1-C10 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C6-C12 aryl group, or two adjacent Rs m are bonded to each other to form a substituted or unsubstituted: cyclopropane ring, cyclobutane ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, cyclobutene ring, cyclopentene ring, cyclohexene ring, cycloheptene ring.
4. An organic electroluminescent device according to claim 1, wherein, Ar is selected from one of the following groups: b0 is selected from integers of 0-4; b is selected from integers of 0-3; b1 is selected from integers of 0-5; b2 is selected from integers of 0-6; b3 is selected from integers of 0-8; b4 is selected from integers of 0-10; b5 is selected from integers of 0-12; R5 is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C2-C18 heteroaryl, substituted or unsubstituted C3-C10 heteroalicyclic group, or two adjacent R5s are bonded to each other to form a substituted or unsubstituted benzene ring, cyclopropane ring, cyclobutane ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, cyclobutene ring, cyclopentene ring, cyclohexene ring, cycloheptene ring, pyridine ring, pyrimidine ring; when there are more than two R5s, each R5 is the same or different from each other; R9 is selected from one of hydrogen, deuterium, tritium, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C3-C10 heteroalicyclic group; when there are more than two R9s, each R9 is the same or different from each other; The R x is the same as or different from one selected from hydrogen, deuterium, tritium, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C2-C18 heteroaryl, "fused ring group of substituted or unsubstituted C3-C10 alicyclic ring and C6-C12 aromatic ring", "fused ring group of substituted or unsubstituted C3-C10 alicyclic ring and C2-C12 heteroaromatic ring", or two adjacent Rs x are bonded to each other to form a substituted or unsubstituted: cyclopropane ring, cyclobutane ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, cyclobutene ring, cyclopentene ring, cyclohexene ring, cycloheptene ring.
5. An organic electroluminescent device according to claim 1, characterized in that, L0 is selected from a single bond or one of the following groups; n is an integer from 0 to 3; when n is 2 or more, each L0 is the same or different from each other; n1 is an integer from 0 to 4; n2 is an integer from 0 to 6; R6 is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C2-C18 heteroaryl, substituted or unsubstituted C3-C10 heteroalicyclic group; when there are more than two R6s, each R6 is the same or different from each other.
6. An organic electroluminescent device according to claim 1, characterized in that, L3 and L4 are independently selected from a single bond or one of the following groups, The Zs are the same or different and are each independently selected from C(R z ), or N, and each R z is the same or different and is each independently selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C2-C18 heteroaryl, substituted or unsubstituted C3-C10 heteroalicyclic group, or two adjacent Rs z are bonded to each other to form a substituted or unsubstituted: benzene ring, cyclopropane ring, cyclobutane ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, cyclobutene ring, cyclopentene ring, cyclohexene ring, cycloheptene ring, pyridine ring, pyrimidine ring.
7. An organic electroluminescent device according to claim 1, wherein R3 and R4 are independently selected from one of the following groups, R7 is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C2-C18 heteroaryl, "fused ring group of substituted or unsubstituted C3-C10 alicyclic ring and C6-C12 aromatic ring", "fused ring group of substituted or unsubstituted C3-C10 alicyclic ring and C2-C12 heteroaromatic ring", substituted or unsubstituted C3-C10 heteroalicyclic group; The R x1 is selected from one of hydrogen, deuterium, tritium, a substituted or unsubstituted C1-C6 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C12 aryl group, a substituted or unsubstituted C2-C18 heteroaryl group, "a fused ring group of a substituted or unsubstituted C3-C10 alicyclic ring and a C6-C12 aromatic ring", "a fused ring group of a substituted or unsubstituted C3-C10 alicyclic ring and a C2-C12 heteroaromatic ring", and a substituted or unsubstituted C3-C10 alicyclic heterocyclic group; c1 is selected from integers from 0 to 4; c2 is selected from integers from 0 to 3; c3 is selected from integers from 0 to 2; R y is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C2-C18 heteroaryl, "fused ring group of substituted or unsubstituted C3-C10 alicyclic ring and C6-C12 aromatic ring", "fused ring group of substituted or unsubstituted C3-C10 alicyclic ring and C2-C12 heteroaromatic ring", substituted or unsubstituted C3-C10 alicyclic heterocyclic group, or two adjacent Rs y are bonded to each other to form a substituted or unsubstituted: benzene ring, cyclopropane ring, cyclobutane ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, cyclobutene ring, cyclopentene ring, cyclohexene ring, cycloheptene ring, pyridine ring, pyrimidine ring; when there are more than two Rs y exist, each R y is the same as or different from each other.
8. An organic electroluminescent device according to claim 1, wherein The triarylamine compound represented by Formula 1 is selected from at least one of the following structures, 9. An organic electroluminescent device according to claim 1, wherein, The heterocyclic compound represented by Formula 2 is selected from at least one of the following structures,
Citation Information
Patent Citations
Heteroanthracene derivative and application thereof, and organic electroluminescent device
CN112390778A
Organic light-emitting device and display device
CN113540371A