Organic electroluminescent device and electronic device
By using specific first compounds and second compounds in the light-emitting layer of the organic electroluminescent device, the problems of high driving voltage, low luminous efficiency and short lifespan in the existing technology are solved, and higher luminous efficiency and more durable life are achieved. Long life.
Patent Information
- Application Number
- CN202310880884.3
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2023-07-18
- Publication Date
- 2025-01-21
- Estimated Expiration
- 2043-07-18
AI Technical Summary
The existing organic electroluminescent devices have problems such as excessive driving voltage, low luminous efficiency or short life, which affects their use areas.
An organic electroluminescent device is used, the main material of the light-emitting layer is composed of a specific first compound and a second compound. The first compound has naphtho[2,1-d]oxazole as an electron transport material connected to triazine through the 9-position, and the second compound has benzocarbazole as the parent core of a compound connected to an arylamine, and the substituent of the arylamine is Contains dibenzofuran/dibenzothiophene or benzoxazole groups. These compounds are mixed in a certain ratio to form a mixed red light host material to improve the carrier balance and film stability of the light-emitting layer.
It significantly improves the carrier balance in the light-emitting layer and improves the stability of the film, thus improving the luminous efficiency and lifespan of the device.
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Figure CN119343035A_ABST
Abstract
Description
Technical Field
[0001] The present application relates to the technical field of organic electroluminescent materials, and in particular to an organic electroluminescent device and an electronic apparatus. Background Art
[0002] In recent years, organic electroluminescent devices (OLEDs) have become a very popular emerging flat-panel display product both at home and abroad. This is because OLED displays have the characteristics of self-luminescence, wide viewing angle, short response time, high efficiency, and wide color gamut.
[0003] An organic electroluminescent device (OLED) generally includes an anode, a cathode, and an organic layer formed between the two electrodes. The organic layer may include a hole injection layer, a hole transport layer, a hole auxiliary layer, an electron blocking layer, a light-emitting layer (containing a host and a dopant material), a hole blocking layer, an electron transport layer, an electron injection layer, etc. If a voltage is applied to the organic electroluminescent device, holes and electrons are injected into the light-emitting layer by the anode and the cathode, respectively. Then, in the light-emitting layer, the injected holes and electrons recombine to form excitons. The excitons are in an excited state and release energy outward, thereby causing the light-emitting layer to emit light outward.
[0004] At present, there are still problems of poor performance in the use of organic electroluminescent devices, such as excessively high driving voltage, low luminous efficiency or short life, which all affect the use field of organic electroluminescent devices. Therefore, it is still necessary to conduct further research in this field to improve the performance of organic electroluminescent devices. Summary of the invention
[0005] In view of the above problems existing in the prior art, the purpose of the present application is to provide an organic electroluminescent device and an electronic device to improve the performance of the device and the device.
[0006] According to a first aspect of the present application, there is provided an organic electroluminescent device, comprising a cathode, an anode and an organic layer;
[0007] Wherein, the cathode and the anode are arranged opposite to each other;
[0008] The organic layer is located between the cathode and the anode;
[0009] The organic layer includes an organic light-emitting layer;
[0010] The organic light-emitting layer includes a first compound and a second compound;
[0011] The first compound has a structure shown in Formula 1
[0012]
[0013] Either X or Z is -N=, and the other is O or S;
[0014] L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 18 carbon atoms;
[0015] L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 12 carbon atoms;
[0016] The substituents in L, L1 and L2 are the same or different and are independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 5 carbon atoms, haloalkyl group having 1 to 5 carbon atoms, deuterated alkyl group having 1 to 5 carbon atoms, trialkylsilyl group having 3 to 8 carbon atoms, aryl group having 6 to 14 carbon atoms, deuterated aryl group having 6 to 12 carbon atoms, heteroaryl group having 3 to 12 carbon atoms or cycloalkyl group having 5 to 10 carbon atoms;
[0017] Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a group represented by formula (X-1) or a group represented by formula (X-2);
[0018]
[0019] Ring A and Ring T are each independently selected from a benzene ring or a naphthalene ring;
[0020] Y is selected from O, S or N(Ar);
[0021] Ar is selected from a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, and the substituents in Ar are the same or different and are each independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, a deuterated aryl group having 6 to 12 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms;
[0022] Ar3 is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
[0023] The substituents in Ar1, Ar2 and Ar3 are the same or different and are independently selected from hydrogen, deuterium, cyano, halogen groups, alkyl groups having 1 to 10 carbon atoms, haloalkyl groups having 1 to 10 carbon atoms, deuterated alkyl groups having 1 to 10 carbon atoms, trialkylsilyl groups having 3 to 12 carbon atoms, triphenylsilyl groups, aryl groups having 6 to 18 carbon atoms, deuterated aryl groups having 6 to 18 carbon atoms, heteroaryl groups having 3 to 18 carbon atoms or cycloalkyl groups having 5 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 5-13 membered ring;
[0024] R1, R2, R3 and R4 are each independently selected from hydrogen, deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 18 carbon atoms, deuterated aryl having 6 to 18 carbon atoms, heteroaryl having 3 to 18 carbon atoms or cycloalkyl having 5 to 10 carbon atoms;
[0025] n1 represents the number of R1, and n1 is selected from 0, 1, 2 or 3;
[0026] n2 represents the number of R2, and n2 is selected from 0, 1 or 2;
[0027] n3 represents the number of R3, and n3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7;
[0028] n4 represents the number of R4, and n4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8;
[0029] The second compound has a structure shown in Formula 2:
[0030]
[0031] Ring Q is a naphthalene ring;
[0032] Ar5 is selected from the group represented by formula (X-3) or the group represented by formula (X-4);
[0033]
[0034] W and V are each independently selected from O or S;
[0035] Ar4, Ar6 and Ar7 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
[0036] L4, L5 and L6 are selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
[0037] The substituents in L4, L5, L6, Ar4, Ar6 and Ar7 are the same or different and are independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, alkylthio group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms or cycloalkyl group having 3 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring;
[0038] R5, R6, R7 and R8 are each independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms or cycloalkyl having 3 to 10 carbon atoms; n5 is selected from 0, 1, 2, 3 or 4; n6 is selected from 0, 1, 2, 3, 4, 5 or 6; n7 is selected from 0, 1, 2 or 3; n8 is selected from 0, 1, 2, 3, 4, 5, 6 or 7.
[0039] According to a second aspect of the present application, an electronic device is provided, comprising the organic electroluminescent device according to the first aspect.
[0040] The main material of the light-emitting layer of the organic electroluminescent device of the present application comprises the first compound and the second compound, wherein the first compound is an electron transport material having naphtho[2,1-d]oxazole connected to triazine via the 9-position, and the second compound is a compound having benzocarbazole as a parent core connected to aromatic amine, wherein the other two substituents of the aromatic amine contain dibenzofuran / dibenzothiophene or benzoxazole groups, and the first compound and the second compound are mixed in a certain ratio to form a mixed red light main material. First, the electron transport material used in the present application has a special connection method. On the one hand, it can maintain a relatively high first triplet energy level value of the material while having a strong carrier transport ability and a high energy transfer ability; on the other hand, this special connection method can make the compound structure have a certain degree of distortion, inhibit excessive stacking between compound molecules, and inhibit the crystallization of the compound, thereby giving the compound film a higher stability; secondly, on the one hand, the hole transport material used in the present application contains a benzocarbazole parent nucleus, and the benzocarbazole parent nucleus has a large conjugated area, which can improve the hole mobility of aromatic amine compounds; on the other hand, benzofuran / dibenzothiophene and benzoxazole groups have certain electron-withdrawing properties compared with aromatic groups. When they are connected to triarylamines, the lowest unoccupied molecular orbital (LUMO) of the molecule can be restricted to the benzofuran / dibenzothiophene or benzoxazole group, thereby improving the electron tolerance of the molecule. Therefore, when the first compound and the second compound of the present application are combined as a mixed red light host material, the carrier balance in the light-emitting layer can be significantly improved, the stability of the film can be improved, and the luminous efficiency and life of the device can be improved. BRIEF DESCRIPTION OF THE DRAWINGS
[0041] The accompanying drawings are used to provide further understanding of the present application and constitute a part of the specification. Together with the following specific embodiments, they are used to explain the present application, but do not constitute a limitation to the present application.
[0042] Figure 1 It is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of the present application.
[0043] Figure 2 It is a schematic diagram of the structure of an electronic device according to an embodiment of the present application.
[0044] Reference numerals
[0045] 100, anode 200, cathode 300, functional layer 310, hole injection layer
[0046] 321, first hole transport layer 322, hole adjustment layer 320, hole transport layer 330, organic light emitting layer
[0047] 340, electron transport layer 350, electron injection layer 400, electronic device DETAILED DESCRIPTION
[0048] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, exemplary embodiments can be implemented in a variety of forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that the present application will be more comprehensive and complete and the concepts of the exemplary embodiments are fully conveyed to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, many specific details are provided to provide a full understanding of the embodiments of the present application.
[0049] In the drawings, the thickness of regions and layers may be exaggerated for clarity. The same reference numerals in the drawings denote the same or similar structures, and thus their detailed description will be omitted.
[0050] According to a first aspect of the present application, there is provided an organic electroluminescent device, comprising a cathode, an anode and an organic layer;
[0051] Wherein, the cathode and the anode are arranged opposite to each other;
[0052] The organic layer is located between the cathode and the anode;
[0053] The organic layer includes an organic light-emitting layer;
[0054] The organic light-emitting layer includes a first compound and a second compound;
[0055] The first compound has a structure shown in Formula 1
[0056]
[0057] Either X or Z is -N=, and the other is O or S;
[0058] L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 18 carbon atoms;
[0059] L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 12 carbon atoms;
[0060] The substituents in L, L1 and L2 are the same or different and are independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 5 carbon atoms, haloalkyl group having 1 to 5 carbon atoms, deuterated alkyl group having 1 to 5 carbon atoms, trialkylsilyl group having 3 to 8 carbon atoms, aryl group having 6 to 14 carbon atoms, deuterated aryl group having 6 to 12 carbon atoms, heteroaryl group having 3 to 12 carbon atoms or cycloalkyl group having 5 to 10 carbon atoms;
[0061] Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a group represented by formula (X-1) or a group represented by formula (X-2);
[0062]
[0063] Ring A and Ring T are each independently selected from a benzene ring or a naphthalene ring;
[0064] Y is selected from O, S or N(Ar);
[0065] Ar is selected from a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, and the substituents in Ar are the same or different and are each independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, a deuterated aryl group having 6 to 12 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms;
[0066] Ar3 is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
[0067] The substituents in Ar1, Ar2 and Ar3 are the same or different and are independently selected from hydrogen, deuterium, cyano, halogen groups, alkyl groups having 1 to 10 carbon atoms, haloalkyl groups having 1 to 10 carbon atoms, deuterated alkyl groups having 1 to 10 carbon atoms, trialkylsilyl groups having 3 to 12 carbon atoms, triphenylsilyl groups, aryl groups having 6 to 18 carbon atoms, deuterated aryl groups having 6 to 18 carbon atoms, heteroaryl groups having 3 to 18 carbon atoms or cycloalkyl groups having 5 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 5-13 membered ring;
[0068] R1, R2, R3 and R4 are each independently selected from hydrogen, deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 18 carbon atoms, deuterated aryl having 6 to 18 carbon atoms, heteroaryl having 3 to 18 carbon atoms or cycloalkyl having 5 to 10 carbon atoms;
[0069] n1 represents the number of R1, and n1 is selected from 0, 1, 2 or 3;
[0070] n2 represents the number of R2, and n2 is selected from 0, 1 or 2;
[0071] n3 represents the number of R3, and n3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7;
[0072] n4 represents the number of R4, and n4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8;
[0073] The second compound has a structure shown in Formula 2:
[0074]
[0075] Ring Q is a naphthalene ring;
[0076] Ar5 is selected from the group represented by formula (X-3) or the group represented by formula (X-4);
[0077]
[0078] W and V are each independently selected from O or S;
[0079] Ar4, Ar6 and Ar7 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
[0080] L4, L5 and L6 are selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
[0081] The substituents in L4, L5, L6, Ar4, Ar6 and Ar7 are the same or different and are independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, alkylthio group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms or cycloalkyl group having 3 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring;
[0082] R5, R6, R7 and R8 are each independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms or cycloalkyl having 3 to 10 carbon atoms; n5 is selected from 0, 1, 2, 3 or 4; n6 is selected from 0, 1, 2, 3, 4, 5 or 6; n7 is selected from 0, 1, 2 or 3; n8 is selected from 0, 1, 2, 3, 4, 5, 6 or 7.
[0083] In the present application, the terms "optionally" and "optionally" mean that the event or environment described subsequently may or may not occur. For example, "optionally, any two adjacent substituents form a saturated or unsaturated 3-15 membered ring" includes: the scenario where any two adjacent substituents form a ring, and the scenario where any two adjacent substituents exist independently and do not form a ring. "Any two adjacent" can include two substituents on the same atom, and can also include two adjacent atoms each having one substituent; wherein, when there are two substituents on the same atom, the two substituents can form a saturated or unsaturated spiro ring with the atom to which they are commonly connected; when there is one substituent on two adjacent atoms respectively, the two substituents can be fused into a ring.
[0084] In this application, the descriptions "each... independently is" and "... are independently" and "... are independently" are interchangeable and should be understood in a broad sense. They can mean that in different groups, the specific options expressed by the same symbols do not affect each other, or in the same group, the specific options expressed by the same symbols do not affect each other. For example, Wherein, each q is independently 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, and chlorine, which means: Formula Q-1 indicates that there are q substituents R" on the benzene ring, and each R" can be the same or different, and the options of each R" do not affect each other; Formula Q-2 indicates that there are q substituents R" on each benzene ring of biphenyl, and the number q of R" substituents on the two benzene rings can be the same or different, and each R" can be the same or different, and the options of each R" do not affect each other.
[0085] In the present application, the term "substituted or unsubstituted" means that the functional group recorded after the term may or may not have a substituent (hereinafter, for the convenience of description, the substituent is collectively referred to as Rc). For example, "substituted or unsubstituted aryl" means an aryl having a substituent Rc or an unsubstituted aryl. The substituent Rc mentioned above may be, for example, deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 20 carbon atoms, deuterated aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, aryloxy having 6 to 20 carbon atoms, or arylthio having 6 to 20 carbon atoms, etc. The number of substitutions may be one or more.
[0086] In the present application, "plurality" means more than 2, for example, 2, 3, 4, 5, 6, etc.
[0087] In the present application, the number of carbon atoms in a substituted or unsubstituted functional group refers to the number of all carbon atoms.
[0088] The hydrogen atoms in the structures of the compounds of the present application include various isotope atoms of the hydrogen element, such as hydrogen (H), deuterium (D) or tritium (T).
[0089] The "D" in the structural formula of the compound of the present application represents deuteration.
[0090] In the present application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. Aryl can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl. In other words, aryl can be a monocyclic aryl, a condensed ring aryl, two or more monocyclic aryl groups connected by carbon-carbon bond conjugation, a monocyclic aryl and a condensed ring aryl connected by carbon-carbon bond conjugation, and two or more condensed ring aryl groups connected by carbon-carbon bond conjugation. That is, unless otherwise specified, two or more aromatic groups connected by carbon-carbon bond conjugation can also be regarded as aryl of the present application. Wherein, condensed ring aryl can, for example, include bicyclic condensed aryl (e.g., naphthyl), tricyclic condensed aryl (e.g., phenanthrenyl, fluorenyl, anthracenyl), etc. Aryl does not contain heteroatoms such as B, N, O, S, P, Se, and Si. Examples of aryl groups include, but are not limited to, phenyl, naphthyl, fluorenyl, spirobifluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, triphenylene, peryl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl, Ji et al.
[0091] In the present application, the arylene group refers to a divalent or multivalent group formed by further losing one or more hydrogen atoms from an aryl group.
[0092] In the present application, terphenyl includes
[0093] In the present application, the carbon number of the substituted or unsubstituted aryl (arylene) group may be 6, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39 or 40. In some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.
[0094] In the present application, the fluorenyl group may be substituted by one or more substituents. When the fluorenyl group is substituted, the substituted fluorenyl group may be: etc., but not limited thereto.
[0095] In the present application, the aryl group as a substituent is exemplified but not limited to phenyl, naphthyl, phenanthrenyl, biphenyl, fluorenyl, dimethylfluorenyl and the like.
[0096] In the present application, heteroaryl refers to a monovalent aromatic ring or a derivative thereof containing 1, 2, 3, 4, 5 or 6 heteroatoms in the ring, and the heteroatoms may be one or more of B, O, N, P, Si, Se and S. The heteroaryl may be a monocyclic heteroaryl or a polycyclic heteroaryl, in other words, the heteroaryl may be a single aromatic ring system or a plurality of aromatic ring systems conjugated by carbon-carbon bonds, and any aromatic ring system may be an aromatic monocyclic ring or an aromatic condensed ring. By way of example, the heteroaryl group may include a thienyl group, a furyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a triazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, an acridinyl group, a pyridazinyl group, a pyrazinyl group, a quinolyl group, a quinazolinyl group, a quinoxalinyl group, a phenoxazinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothienyl group, a dibenzothienyl group, a thienothiphenyl group, a benzofuranyl group, a phenanthrolinyl group, an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, a silyfluorenyl group, a dibenzofuranyl group, and an N-phenylcarbazolyl group, an N-pyridylcarbazolyl group, an N-methylcarbazolyl group, and the like, without being limited thereto.
[0097] In the present application, the heteroarylene group refers to a divalent or multivalent group formed by further losing one or more hydrogen atoms from a heteroaryl group.
[0098] In the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl (heteroarylene) can be selected from 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39 or 40. In some embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl with a total carbon number of 3 to 30, in other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl with a total carbon number of 12 to 18, and in other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl with a total carbon number of 5 to 12.
[0099] In the present application, the heteroaryl group as a substituent is, for example but not limited to, pyridyl, carbazolyl, dibenzothiophenyl, dibenzofuranyl, benzoxazolyl, benzothiazolyl, and benzimidazolyl.
[0100] In the present application, the substituted heteroaryl group may be a heteroaryl group in which one or more hydrogen atoms are replaced by groups such as a deuterium atom, a halogen group, -CN, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, a cycloalkyl group, a haloalkyl group, and the like.
[0101] In the present application, the alkyl group having 1 to 10 carbon atoms may include a straight-chain alkyl group having 1 to 10 carbon atoms and a branched-chain alkyl group having 3 to 10 carbon atoms. The number of carbon atoms in the alkyl group may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, and specific examples of the alkyl group include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, and the like.
[0102] In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.
[0103] In the present application, specific examples of trialkylsilyl include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.
[0104] In the present application, specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.
[0105] In the present application, the carbon number of the cycloalkyl group having 3 to 10 carbon atoms may be, for example, 3, 4, 5, 6, 7, 8 or 10. Specific examples of the cycloalkyl group include, but are not limited to, cyclopentyl, cyclohexyl, and adamantyl.
[0106] In the present application, the carbon number of the deuterated alkyl group having 1 to 10 carbon atoms is, for example, 1, 2, 3, 4, 5, 6, 7, 8 or 10. Specific examples of the deuterated alkyl group include, but are not limited to, trideuterated methyl group.
[0107] In the present application, the carbon number of the haloalkyl group having 1 to 10 carbon atoms is, for example, 1, 2, 3, 4, 5, 6, 7, 8 or 10. Specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.
[0108] In the present application, a ring system formed by n atoms is an n-membered ring. For example, phenyl is a 6-membered ring. A 3-15-membered ring refers to a cyclic group having 3-15 ring atoms. Examples of 3-15-membered rings include cyclopentane, cyclohexane, fluorene ring, benzene ring, etc.
[0109] In this application, Refers to the chemical bonds that connect to other groups.
[0110] In this application, no single bond extending from the ring system is involved in the positioning of the connecting bond. It means that one end of the connecting bond can be connected to any position in the ring system that the bond passes through, and the other end is connected to the rest of the compound molecule. For example, as shown in the following formula (f), the naphthyl represented by formula (f) is connected to other positions of the molecule through two non-positional connecting bonds that pass through the bicyclic ring. The meaning represented by it includes any possible connection mode shown in formula (f-1) to formula (f-10):
[0111]
[0112] For another example, as shown in the following formula (X'), the dibenzofuranyl represented by formula (X') is connected to other positions of the molecule through a non-positional connecting bond extending from the middle of one side of the benzene ring, and the meaning represented by it includes any possible connection mode shown in formula (X'-1) to formula (X'-4):
[0113]
[0114] The non-positioning substituent in the present application refers to a substituent connected by a single bond extending from the center of the ring system, which means that the substituent can be connected to any possible position in the ring system. For example, as shown in the following formula (Y), the substituent R' represented by formula (Y) is connected to the quinoline ring through a non-positioning connecting bond, and the meaning represented by it includes any possible connection mode shown in formula (Y-1) to formula (Y-7):
[0115]
[0116] In some embodiments, the compound represented by Formula 1 is selected from the following structures represented by Formulas (1-1) to (1-2):
[0117]
[0118] In some embodiments, in the first compound represented by Formula 1, L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17 or 18 carbon atoms.
[0119] In some embodiments, in the first compound represented by Formula 1, L is selected from a single bond, a substituted or unsubstituted arylene group having 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5, 6, 7, 8, 9, 10 or 12 carbon atoms.
[0120] Optionally, the substituents in L, L1 and L2 are the same or different and are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, a trialkylsilyl group having 3 to 7 carbon atoms, a phenyl group or a deuterated phenyl group.
[0121] In some embodiments, in the first compound of Formula 1, L, L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group or a substituted or unsubstituted pyridinyl group;
[0122] Optionally, the substituents in L, L1 and L2 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, pentadeuterated phenyl or phenyl.
[0123] In some embodiments, in the first compound represented by Formula 1, L1 and L2 are each independently selected from a single bond or the group consisting of the following groups:
[0124]
[0125] L is selected from a single bond or the group consisting of:
[0126]
[0127] In some embodiments, in the first compound of Formula 1, L, L1 and L2 are each independently selected from a single bond or the group consisting of the following groups:
[0128]
[0129]
[0130] In some embodiments, in the first compound shown in Formula 1, Ar1 and Ar2 are each independently selected from a substituted or unsubstituted aromatic group having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30 carbon atoms, a group shown in Formula (X-1) or a group shown in Formula (X-2).
[0131] Optionally, the substituents in Ar1 and Ar2 are each independently selected from deuterium, a halogen group, a cyano group, a haloalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 15 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, or a deuterated aryl group having 6 to 15 carbon atoms, and optionally, any two adjacent substituents form a benzene ring or a fluorene ring.
[0132] In some embodiments, in the first compound represented by Formula 1, Ar1 and Ar2 are the same or different, and are each independently selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted pyrene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted spirobifluorenyl group, a group represented by Formula (X-1), or a group represented by Formula (X-2);
[0133] The substituents in Ar1 and Ar2 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuterophenyl, phenyl or naphthyl;
[0134]
[0135] Alternatively, in formula (X-1) and formula (X-2), ring A and ring T are each independently selected from a benzene ring or a naphthalene ring;
[0136] Y is selected from O, S or N(Ar);
[0137] Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl;
[0138] The substituents in Ar, each R3 and R4 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, pentadeuterated phenyl or phenyl.
[0139] In some embodiments, in the first compound shown in Formula 1, Ar1 and Ar2 are the same or different, and are each independently selected from a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted phenanthrenyl, a substituted or unsubstituted anthracenyl, a substituted or unsubstituted pyrenyl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted spirobifluorenyl or the following groups:
[0140]
[0141]
[0142] The substituents in Ar1 and Ar2 and each of R3 and R4 are the same or different and are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuterated methyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, pentadeuterated phenyl or naphthyl;
[0143] n3 represents the number of R3, and n3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7;
[0144] n4 represents the number of R4, and n4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.
[0145] In some more specific embodiments, in the first compound represented by Formula 1, Ar1 and Ar2 are the same or different and are each independently selected from the following groups:
[0146]
[0147] In some embodiments, in the first compound represented by Formula 1, Ar1 and Ar2 are the same or different and are each independently selected from the following groups:
[0148]
[0149]
[0150] In some embodiments, in the first compound shown in Formula 1, Ar3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, and the substituents in Ar3 are the same or different and are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuterated methyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, pentadeuterated phenyl or naphthyl.
[0151] In some embodiments, in the first compound of Formula 1, Ar3 is selected from the following groups:
[0152]
[0153] In some embodiments, in the first compound represented by Formula 1, Ar3 is selected from the following groups:
[0154]
[0155]
[0156] In some embodiments, in the first compound represented by Formula 1, Each is independently selected from the following groups:
[0157]
[0158] In some embodiments, in the first compound of Formula 1, each R1 and R2 is independently selected from hydrogen, deuterium, fluorine, cyano, trimethylsilyl, trideuterated methyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, pentadeuterated phenyl or naphthyl.
[0159] In some embodiments, the second compound represented by Formula 2 is selected from the structures represented by the following formulas (2-1) to (2-3):
[0160]
[0161] In some embodiments, in the second compound shown in Formula 2, Ar4 and Ar7 are each independently selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.
[0162] Optionally, the substituents in Ar4 and Ar7 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, triphenylsilyl, trideuterated methyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl.
[0163] In some embodiments, in the second compound represented by Formula 2, Ar4 and Ar7 are each independently selected from the following groups:
[0164]
[0165] In some embodiments, in the second compound represented by Formula 2, Ar4 and Ar7 are each independently selected from the following groups:
[0166]
[0167] In some embodiments, in the second compound represented by Formula 2, L4, L5 and L6 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17 or 18 carbon atoms.
[0168] Optionally, the substituents in L4, L5 and L6 are the same or different and are each independently selected from deuterium, fluorine, cyano, alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms, deuterated alkyl having 1 to 4 carbon atoms, trialkylsilyl having 3 to 7 carbon atoms or phenyl.
[0169] In some embodiments, in the second compound shown in Formula 2, L4, L5 and L6 are each independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted fluorenylene, a substituted or unsubstituted phenanthrenylene, a substituted or unsubstituted anthraceneylene, a substituted or unsubstituted carbazolylene, a substituted or unsubstituted dibenzothiophenylene, and a substituted or unsubstituted dibenzofuranylene.
[0170] Optionally, the substituents in L4, L5 and L6 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuterated methyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.
[0171] In some embodiments, in the second compound represented by Formula 2, L4 and L5 are each independently selected from a single bond or the following groups:
[0172]
[0173] In some embodiments, in the second compound represented by Formula 2, L6 is selected from a single bond or the following groups:
[0174]
[0175] In some embodiments, in the second compound shown in Formula 2, when Ar5 is selected from the structure shown in Formula (X-3), L5 is selected from substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, and the substituents in L5 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuterated methyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.
[0176] In some embodiments, in the second compound shown in Formula 2, when Ar5 is selected from the structure shown in Formula (X-4), L5 is selected from a single bond, a substituted or unsubstituted phenylene or a substituted or unsubstituted naphthylene, and the substituents in L5 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuterated methyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.
[0177] In some embodiments, in the second compound represented by Formula 2, Ar6 is selected from substituted or unsubstituted aryl having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30 carbon atoms, and substituted or unsubstituted heteroaryl having 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30 carbon atoms.
[0178] Optionally, the substituents in Ar6 are each independently selected from deuterium, a halogen group, a cyano group, a haloalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 15 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, or a deuterated aryl group having 6 to 15 carbon atoms, and optionally, any two adjacent substituents form a benzene ring or a fluorene ring.
[0179] In some embodiments, in the second compound shown in Formula 2, Ar6 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyrene, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, and substituted or unsubstituted carbazolyl.
[0180] Optionally, the substituents in Ar6 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, triphenylsilyl, trideuterated methyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl.
[0181] In some embodiments, in the second compound represented by Formula 2, Ar6 is selected from the following groups:
[0182]
[0183] In some embodiments, in the second compound represented by Formula 2, Ar6 is selected from the following groups:
[0184]
[0185]
[0186] In some embodiments, in the second compound represented by Formula 2, Ar5 is selected from the following groups:
[0187]
[0188] In some embodiments, in the second compound represented by Formula 2, Selected from the group consisting of:
[0189]
[0190] In some embodiments, in the second compound represented by Formula 2, each R5 and R6 is independently selected from hydrogen, deuterium, fluorine, cyano, trimethylsilyl, trideuterated methyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, pentadeuterated phenyl or naphthyl.
[0191] In some embodiments, the first compound is selected from the compounds shown in A-1 to A-336 in claim 14.
[0192] In some embodiments, the second compound is selected from the compounds shown as B-1- to B-282 and C-1 to C-252 in claim 14.
[0193] Further, in the organic electroluminescent device of the present application, the organic light-emitting layer comprises a host material and a dopant. The host material comprises a first compound and a second compound. Generally, based on the weight (mass) of the two compounds, the mass ratio of the first compound to the second compound is 1:99 to 99:1, preferably 10:90 to 90:10, further preferably 30:70 to 70:30, and more preferably 40:60 to 60:40. Further, the mass ratio of the host material to the dopant in the organic light-emitting layer is 90:10 to 99:1.
[0194] In some embodiments, the mass ratio of the first compound (the compound of Formula 1) to the second compound (the compound of Formula 2) in the light-emitting layer host of the organic electroluminescent device is 30:70 to 70:30.
[0195] Optionally, in the host material, the mass ratio of the first compound (compound of formula 1) to the second compound (compound of formula 2) is 35:65, 40:60, 45:55, 50:50, 55:45, 60:40, or 65:35.
[0196] In order to obtain the host material mixture, the first compound and the second compound may be placed in an oscillator and mixed to obtain a mixture with a desired weight ratio.
[0197] In order to form each layer constituting the organic electroluminescent device of the present application, a dry film-forming method such as vacuum deposition, sputtering, plasma, ion plating method, etc., or a wet film-forming method such as inkjet printing, nozzle printing, slit coating, spin coating, dip coating, flow coating method, etc. can be used.
[0198] In addition, the first compound and the second compound can be subjected to film formation in the above-listed methods, usually by a co-evaporation method or a hybrid evaporation method. Co-evaporation is a hybrid deposition method in which two or more materials are placed in a corresponding single crucible source and current is applied to multiple chambers simultaneously to evaporate the materials. Hybrid evaporation is a hybrid deposition method in which two or more materials are mixed in one crucible source before evaporation and current is applied to the chambers to evaporate the materials.
[0199] In some embodiments of the present application, the organic electroluminescent device is a phosphorescent device.
[0200] In some specific embodiments of the present application, the organic electroluminescent device is a green organic electroluminescent device or a red organic electroluminescent device.
[0201] In a second aspect of the present application, an electronic device is provided, wherein the electronic device comprises the organic electroluminescent device described in the first aspect.
[0202] In another aspect of the present application, a composition is also provided, the composition comprising a first compound and a second compound, the first compound having a structure shown in Formula 1
[0203]
[0204] Either X or Z is -N=, and the other is O or S;
[0205] L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 18 carbon atoms;
[0206] L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 12 carbon atoms;
[0207] The substituents in L, L1 and L2 are the same or different and are independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 5 carbon atoms, haloalkyl group having 1 to 5 carbon atoms, deuterated alkyl group having 1 to 5 carbon atoms, trialkylsilyl group having 3 to 8 carbon atoms, aryl group having 6 to 14 carbon atoms, deuterated aryl group having 6 to 12 carbon atoms, heteroaryl group having 3 to 12 carbon atoms, and cycloalkyl group having 5 to 10 carbon atoms;
[0208] Ar1 and Ar2 are the same or different and are independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a group represented by formula X-1 or a group represented by formula X-2;
[0209]
[0210] Ring A and Ring T are each independently selected from a benzene ring or a naphthalene ring;
[0211] Y is selected from O, S or N(Ar);
[0212] Ar is selected from a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms;
[0213] The substituents in Ar are the same or different and are independently selected from deuterium, cyano, halogen groups, alkyl groups having 1 to 5 carbon atoms, deuterated alkyl groups having 1 to 5 carbon atoms, haloalkyl groups having 1 to 5 carbon atoms, trialkylsilyl groups having 3 to 8 carbon atoms, aryl groups having 6 to 12 carbon atoms, deuterated aryl groups having 6 to 12 carbon atoms, heteroaryl groups having 3 to 12 carbon atoms or cycloalkyl groups having 5 to 10 carbon atoms;
[0214] Ar3 is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
[0215] The substituents in Ar1, Ar2 and Ar3 are the same or different and are independently selected from hydrogen, deuterium, cyano, halogen groups, alkyl groups having 1 to 10 carbon atoms, haloalkyl groups having 1 to 10 carbon atoms, deuterated alkyl groups having 1 to 10 carbon atoms, trialkylsilyl groups having 3 to 12 carbon atoms, triphenylsilyl groups, aryl groups having 6 to 18 carbon atoms, deuterated aryl groups having 6 to 18 carbon atoms, heteroaryl groups having 3 to 18 carbon atoms or cycloalkyl groups having 5 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 5-13 membered ring;
[0216] R1, R2, R3 and R4 are independently selected from hydrogen, deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 18 carbon atoms, deuterated aryl having 6 to 18 carbon atoms, heteroaryl having 3 to 18 carbon atoms or cycloalkyl having 5 to 10 carbon atoms;
[0217] n1 represents the number of R1, and n1 is selected from 0, 1, 2 or 3;
[0218] n2 represents the number of R2, and n2 is selected from 0, 1 or 2;
[0219] n3 represents the number of R3, and n3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7;
[0220] n4 represents the number of R4, and n4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8;
[0221] The second compound has a structure shown in Formula 2:
[0222]
[0223] Ring Q is a naphthalene ring;
[0224] Ar5 is selected from the group represented by formula X-3 or the group represented by formula X-4;
[0225]
[0226] W and V are each independently selected from O or S;
[0227] Ar4, Ar6 and Ar7 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
[0228] L4, L5 and L6 are selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
[0229] The substituents in L4, L5, L6, Ar4, Ar6 and Ar7 are the same or different and are independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, alkylthio group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms or cycloalkyl group having 3 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring;
[0230] R5, R6, R7 and R8 are each independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms or cycloalkyl having 3 to 10 carbon atoms; n5 is selected from 0, 1, 2, 3 or 4; n6 is selected from 0, 1, 2, 3, 4, 5 or 6; n7 is selected from 0, 1, 2 or 3; n8 is selected from 0, 1, 2, 3, 4, 5, 6 or 7.
[0231] Optionally, the mass ratio of the first compound to the second compound in the composition is 1:99 to 99:1, preferably 10:90 to 90:10, further preferably 30:70 to 70:30, and more preferably 40:60 to 60:40.
[0232] In some embodiments, the mass ratio of the first compound (the compound of Formula 1) to the second compound (the compound of Formula 2) in the composition is 30:70 to 70:30.
[0233] The present application also provides use of the light-emitting layer composition in a light-emitting layer of an organic electroluminescent device.
[0234] The present application also provides an organic electroluminescent device comprising the composition.
[0235] The organic electroluminescent device provided in the present application comprises an anode and a cathode arranged opposite to each other, the cathode, the anode and an organic layer. The organic layer comprises an organic light-emitting layer, and the organic light-emitting layer comprises a first compound and a second compound.
[0236] In some embodiments of the present application, the organic electroluminescent device includes an anode (e.g., ITO / Ag / ITO substrate), a hole transport layer, a hole adjustment layer, an organic light emitting layer, an electron transport layer, an electron injection layer, a cathode (e.g., a Mg-Ag mixture), and an organic covering layer in sequence. The hole transport layer is located between the anode and the organic light emitting layer, and the hole adjustment layer is located between the hole transport layer and the organic light emitting layer.
[0237] According to a specific implementation mode, Figure 1 As shown, the organic electroluminescent device includes an anode 100, a hole injection layer 310, a first hole transport layer 321, a hole adjustment layer (also called a hole auxiliary layer) 322, an organic light-emitting layer 330, an electron transport layer 340, an electron injection layer 350 and a cathode 200 which are stacked in sequence.
[0238] In the present application, the anode 100 includes an anode material, which is preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); combined metals and oxides such as ZnO:Al or SnO2:Sb; or conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline, but not limited thereto. Preferably, a transparent electrode comprising indium tin oxide (indium tin oxide) (ITO) as an anode is included.
[0239] In the present application, the hole transport layer or the hole adjustment layer may include one or more hole transport materials, respectively. The hole transport layer material may be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compounds, and may be specifically selected from the following compounds or any combination thereof:
[0240]
[0241]
[0242] In one embodiment, the first hole transport layer 321 is composed of HT-1.
[0243] In one embodiment, the hole-regulating layer 322 is composed of HT-2.
[0244] Optionally, a hole injection layer 310 is further provided between the anode 100 and the hole transport layer 321 to enhance the ability to inject holes into the hole transport layer 321. The hole injection layer 310 may be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, and the present application does not impose any particular limitation thereto. The material of the hole injection layer 310 may be selected from the following compounds or any combination thereof, for example;
[0245]
[0246] In one embodiment of the present application, the hole injection layer 310 is composed of PD and HT-1.
[0247] Optionally, the organic light-emitting layer 330 may include the host material and the guest material. Optionally, the organic light-emitting layer 330 is composed of the host material and the guest material, and the holes injected into the organic light-emitting layer 330 and the electrons injected into the organic light-emitting layer 330 may be recombined in the organic light-emitting layer 330 to form excitons, and the excitons transfer energy to the host material, and the host material transfers energy to the guest material, thereby enabling the guest material to emit light.
[0248] The host material of the organic light emitting layer 330 includes the first compound and the second compound.
[0249] The guest material of the organic light-emitting layer 330 can be a compound having a condensed aromatic ring or a derivative thereof, a compound having a heteroaromatic ring or a derivative thereof, an aromatic amine derivative or other materials, and the present application does not impose any special restrictions on this. The guest material is also called a doping material or a dopant. According to the type of light emission, it can be divided into a fluorescent dopant and a phosphorescent dopant. For example, specific examples of the phosphorescent dopant include, but are not limited to,
[0250]
[0251]
[0252] In one embodiment of the present application, the organic electroluminescent device is a red organic electroluminescent device. In a more specific embodiment, the host material of the organic light-emitting layer 330 is composed of the first compound and the second compound. The guest material may be RD, for example.
[0253] In another embodiment, the organic electroluminescent device is a green organic electroluminescent device. In a more specific embodiment, the host material of the organic light-emitting layer 330 is composed of the first compound and the second compound. The guest material may be, for example, fac-Ir(ppy)3.
[0254] The electron transport layer 340 may be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials, which may be selected from but not limited to BmPyPhB, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, triazine derivatives and other electron transport materials, and this application does not specifically limit this. The material of the electron transport layer 340 includes LiQ and other electron transport materials, and the other electron transport materials may be selected from but not limited to the following compounds:
[0255]
[0256] In one embodiment of the present application, the electron transport layer 340 is composed of ET-1 and LiQ.
[0257] In the present application, cathode 200 includes a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or their alloys; or multilayer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al and BaF2 / Ca. Optionally, a metal electrode containing magnesium and silver is included as the cathode.
[0258] Optionally, an electron injection layer 350 is further provided between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include a complex of an alkali metal and an organic substance. In one embodiment of the present application, the electron injection layer 350 includes ytterbium (Yb).
[0259] The present application not only provides the organic electroluminescent device comprising the compound represented by Formula 1 and the compound represented by Formula 2 for the organic light emitting layer, but also provides an electronic device comprising the organic electroluminescent device of the present application.
[0260] According to one embodiment, Figure 2 As shown, the provided electronic device is an electronic device 400. The electronic device 400 may be, for example, a display device, a lighting device, an optical communication device or other types of electronic devices, such as but not limited to a computer screen, a mobile phone screen, a television, an electronic paper, an emergency lighting lamp, an optical module, etc.
[0261] The synthesis methods of the first compound and the second compound of the present application are specifically described below in conjunction with synthesis examples, but the present application is not limited thereto.
[0262] Synthesis Example
[0263] Those skilled in the art will recognize that the chemical reactions described herein can be used to appropriately prepare many of the heterocyclic compounds of the present invention, and that other methods for preparing the compounds of the present invention are considered to be within the scope of the present invention. For example, the synthesis of the compounds not exemplified herein can be successfully accomplished by those skilled in the art by modification methods, such as appropriate protection of interfering groups, by utilizing other known reagents in addition to those described herein, or by making some conventional modifications to the reaction conditions. The compounds for which the synthesis methods are not mentioned in the present invention are all raw materials obtained from commercial sources.
[0264] Synthesis of the first compound:
[0265] Synthesis of Sub-a1:
[0266]
[0267] Under nitrogen atmosphere, RM-1 (16.21 g, 50 mmol), diboronic acid pinacol ester (14.0 g, 55 mmol), potassium acetate (10.8 g, 110 mmol) and 1,4-dioxane (160 mL) were added to a 500 mL three-necked flask in sequence, stirring and heating were started, and when the system was heated to 40 ° C, tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 0.46 g, 0.50 mmol) and 2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl (XPhos, 0.48 g, 1.0 mmol) were quickly added, and the temperature was continued to rise to reflux, and the reaction was stirred overnight. After the system was cooled to room temperature, 200 mL of water was added to the system, and the mixture was stirred for 30 min. The mixture was filtered under reduced pressure. The filter cake was washed with deionized water until neutral, and then rinsed with 100 mL of anhydrous ethanol to obtain a gray solid. The crude product was slurried once with n-heptane, dissolved with 200 mL of toluene, and passed through a silica gel column. After concentration, a white solid Sub-a1 (13.55 g, yield 73%) was obtained.
[0268] Synthesis of Sub-b1:
[0269]
[0270] Under nitrogen atmosphere, RM-2 (17.20 g, 50 mmol), 4-chlorophenylboronic acid (8.60 g, 55 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (140 mL), anhydrous ethanol (35 mL) and deionized water (35 mL) were added to a 500 mL three-necked flask in sequence, stirring and heating were started, and the temperature was raised to reflux reaction for 8 h. After the system was cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times), the organic phases were combined and dried with anhydrous magnesium sulfate, filtered and the solvent was removed by reduced pressure distillation to obtain a crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain an orange-yellow solid (16.2 g, yield 77%).
[0271] Referring to the synthesis of Sub-c1, reactant A shown in Table 1 was used to replace RM-2, and reactant B was used to replace 4-chlorophenylboronic acid to synthesize Sub-b2 to Sub-b14.
[0272] Table 1: Synthesis of Sub-b2 to Sub-b14
[0273]
[0274]
[0275] Synthesis of compound A-4:
[0276]
[0277] Under nitrogen atmosphere, add Sub-a1 (9.75 g, 26.25 mmol), RM-3 (8.60 g, 25 mmol), palladium acetate (42 mg, 0.25 mmol), 2-dicyclohexylphosphine-2', 4', 6'triisopropylbiphenyl (XPhos, 0.24 g, 0.5 mmol), anhydrous potassium carbonate (6.9 g, 50 mmol), tetrabutylammonium bromide (0.8 g, 2.5 mmol), toluene (100 mL), tetrahydrofuran (25 mL) and deionized water (25 mL) to a 250 mL three-necked flask in sequence, start stirring and heating, and heat to reflux for 16 h. After the system is cooled to room temperature, extract with dichloromethane (100 mL × 3 times), combine the organic phases and dry with anhydrous magnesium sulfate, filter and remove the solvent by reduced pressure distillation to obtain a crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain a white solid (9.0 g, yield 65%, m / z = 553.20 [M+H] + ).
[0278] Referring to the synthesis of compound A-4, reactant C shown in Table 2 was used instead of RM-3 to synthesize the first compound of the present application in Table 2.
[0279] Table 2: Synthesis of the first compound of the present application
[0280]
[0281]
[0282]
[0283]
[0284]
[0285]
[0286] Synthesis of the second compound:
[0287] Synthesis of Sub-c1:
[0288]
[0289] Under nitrogen atmosphere, RM-4 (18.62 g, 50 mmol), 3-aminodibenzofuran (9.16 g, 50 mmol), tris(dibenzylideneacetone)dipalladium (0.916 g, 1 mmol), (2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl) (XPhos, 0.95 g, 2 mmol), sodium tert-butoxide (9.61 g, 100 mmol) and toluene (180 mL) were added to a 500 mL three-necked flask in sequence, the temperature was raised to reflux, and the reaction was stirred overnight; after the system was cooled to room temperature, the reaction solution was poured into 250 mL of deionized water, stirred thoroughly for 30 min, filtered, and the filter cake was rinsed with deionized water until neutral, and then rinsed with anhydrous ethanol (100 mL); the filter cake was recrystallized from toluene to obtain a gray-green solid Sub-c1 (19.70 g; yield 83%).
[0290] Referring to Sub-c1, reactant D shown in Table 3 was used instead of RM-4, and reactant E was used instead of 3-aminodibenzofuran to synthesize Sub-c2 to Sub-c22.
[0291] Table 3: Synthesis of Sub-c2 to Sub-c22
[0292]
[0293]
[0294]
[0295] Synthesis of compound B-3:
[0296]
[0297] Under nitrogen atmosphere, Sub-c1 (11.86 g, 25 mmol), RM-5 (6.66 g, 27.5 mmol), tris(dibenzylideneacetone)dipalladium (0.46 g, 0.5 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (Sphos, 0.41 g, 1 mmol), sodium tert-butoxide (4.80 g, 50 mmol) and xylene (xylene, 120 mL) were added to a 250 mL three-necked flask in sequence, and the temperature was raised to reflux, and the reaction was stirred overnight; after the system was cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times), the organic phases were combined and dried over anhydrous magnesium sulfate, filtered and the solvent was removed by reduced pressure distillation to obtain a crude product. The crude product was purified by silica gel column chromatography using n-heptane as the mobile phase to obtain a white solid compound B-3 (13.20 g, yield 83%, m / z = 636.30 [M+H] + ).
[0298] Referring to the synthesis of compound B-3, reactant F shown in Table 4 was used to replace Sub-c1, and reactant G was used to replace RM-5 to synthesize the compounds of the present application in Table 4.
[0299] Table 4: Synthesis of the second compound of the present application
[0300]
[0301]
[0302]
[0303]
[0304]
[0305]
[0306] Compound A-242 NMR: 1 H-NMR (400MHz, CD2Cl2) δppm: 9.36 (s, 1H), 8.86-8.78 (m, 4H), 8.57 (d, 1H), 8.04 (d, 1H), 7 .95-7.84(m,7H),7.77(t,1H),7.70-7.44(m,9H),7.41(d,1H),7.18(t,1H),7.08(t,2H);
[0307] Compound B-34 NMR: 1 H-NMR (400MHz, CD2Cl2) δppm: 8.76(d,1H),8.44(d,1H),7.99(d,1H),7.84(d,1H),7.79(d,1H),7.74-7.6 6(m,2H),7.56-7.40(m,8H),7.38-7.26(m,6H),7.20-7.11(m,5H),7.09-6.97(m,5H),6.93-6.83(m,3H);
[0308] NMR of compound C-5: 1H-NMR (400MHz, CD2Cl2) δppm 8.68 (d, 1H), 8.33 (d, 1H), 8.23 (d, 2H), 7.97 (d, 1H), 7.79-7.60 (m, 5H), 7.58-7.32 (m, 16H), 7.24 (d, 2H), 7.12-7.03 (m, 5H), 7.00 (d, 1H), 6.90 (s, 1H).
[0309] Preparation and evaluation of organic electroluminescent devices:
[0310] Example 1: Preparation of red organic electroluminescent device
[0311] First, the anode pretreatment is carried out through the following process: the thickness is On the ITO / Ag / ITO substrate, the surface treatment was carried out using ultraviolet ozone and O2:N2 plasma to increase the work function of the anode, and the surface of the ITO substrate was cleaned with an organic solvent to remove impurities and oil stains on the surface of the ITO substrate.
[0312] PD:HT-1 was co-evaporated on the experimental substrate (anode) at an evaporation rate ratio of 3%:97% to form a layer with a thickness of The hole injection layer (HIL) is then vacuum-deposited with HT-1. The first hole transport layer is formed by a plurality of holes.
[0313] Compound HT-2 is vacuum-deposited on the first hole transport layer to form a layer with a thickness of The second hole transport layer is
[0314] Next, on the second hole transport layer, compound A-4 was used as the first host, compound B-177 was used as the second host, and RD was used as the dopant, and a red light emitting layer was prepared by a co-evaporation method. The first host and the second host were mixed uniformly in a weight ratio of 50:50 to obtain a composition; the composition of the host material and RD were simultaneously evaporated at an evaporation rate ratio of 98%:2% to form a layer with a thickness of The red light emitting layer (EML)
[0315] On the light-emitting layer, compound ET-1 and LiQ were co-evaporated at an evaporation rate ratio of 1:1 to form A thick electron transport layer (ETL) is formed by evaporating Yb on the electron transport layer to form a layer with a thickness of Then, magnesium (Mg) and silver (Ag) were mixed at a evaporation rate of 1:9 and vacuum evaporated on the electron injection layer to form a layer with a thickness of cathode.
[0316] In addition, the thickness of the vacuum evaporation layer on the cathode is CP, thereby completing the manufacture of the red organic electroluminescent device.
[0317] Embodiments 2 to 40
[0318] An organic electroluminescent device was prepared in the same manner as in Example 1, except that the compound combination in Example 1 was replaced by the compound combination in Table 5 below when preparing the light-emitting layer.
[0319] Comparative Examples 1 to 4
[0320] An organic electroluminescent device was prepared by the same method as in Example 1, except that the light-emitting layer host combinations shown in Table 5 below were used instead of the combination of compounds A4 and B-177 in Example 1 when preparing the light-emitting layer.
[0321] Among them, when preparing each embodiment and comparative example, the compound structure used is as follows:
[0322]
[0323] The performance of the red organic electroluminescent devices prepared in Examples 1 to 40 and Comparative Examples 1 to 4 was tested. Specifically, at 10 mA / cm 2 The IVL performance of the device was tested under the conditions of T95 device life at 20mA / cm 2 The test was carried out under the conditions of , and the test results are shown in Table 5.
[0324] Table 5
[0325]
[0326]
[0327] Referring to Table 5 above, it can be seen that when the compound of the present invention is used as the main material of the red organic electroluminescent device, the efficiency is increased by at least 11.9% and the life is increased by at least 10.8%.
[0328] The preferred embodiments of the present invention are described in detail above in conjunction with the accompanying drawings. However, the present invention is not limited to the specific details in the above embodiments. Within the technical concept of the present invention, a variety of simple modifications can be made to the technical solution of the present invention, and these simple modifications all belong to the protection scope of the present invention.
Claims
1. An organic electroluminescent device comprising a cathode, an anode and an organic layer; in, The cathode and the anode are arranged opposite to each other; The organic layer is located between the cathode and the anode; The organic layer includes an organic light-emitting layer; The organic light-emitting layer includes a first compound and a second compound; The first compound has a structure shown in Formula 1 Either X or Z is -N=, and the other is O or S; L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 18 carbon atoms; L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 12 carbon atoms; The substituents in L, L1 and L2 are the same or different and are independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 5 carbon atoms, haloalkyl group having 1 to 5 carbon atoms, deuterated alkyl group having 1 to 5 carbon atoms, trialkylsilyl group having 3 to 8 carbon atoms, aryl group having 6 to 14 carbon atoms, deuterated aryl group having 6 to 12 carbon atoms, heteroaryl group having 3 to 12 carbon atoms or cycloalkyl group having 5 to 10 carbon atoms; Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a group represented by formula (X-1) or a group represented by formula (X-2); Ring A and Ring T are each independently selected from a benzene ring or a naphthalene ring; Y is selected from O, S or N(Ar); Ar is selected from a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, and the substituents in Ar are the same or different and are each independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, a deuterated aryl group having 6 to 12 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms; Ar3 is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; The substituents in Ar1, Ar2 and Ar3 are the same or different and are independently selected from hydrogen, deuterium, cyano, halogen groups, alkyl groups having 1 to 10 carbon atoms, haloalkyl groups having 1 to 10 carbon atoms, deuterated alkyl groups having 1 to 10 carbon atoms, trialkylsilyl groups having 3 to 12 carbon atoms, triphenylsilyl groups, aryl groups having 6 to 18 carbon atoms, deuterated aryl groups having 6 to 18 carbon atoms, heteroaryl groups having 3 to 18 carbon atoms or cycloalkyl groups having 5 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 5-13 membered ring; R1, R2, R3 and R4 are each independently selected from hydrogen, deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 18 carbon atoms, deuterated aryl having 6 to 18 carbon atoms, heteroaryl having 3 to 18 carbon atoms or cycloalkyl having 5 to 10 carbon atoms; n1 represents the number of R1, and n1 is selected from 0, 1, 2 or 3; n2 represents the number of R2, and n2 is selected from 0, 1 or 2; n3 represents the number of R3, and n3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; n4 represents the number of R4, and n4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; The second compound has a structure shown in Formula 2: Ring Q is a naphthalene ring; Ar5 is selected from the group represented by formula (X-3) or the group represented by formula (X-4); W and V are each independently selected from O or S; Ar4, Ar6 and Ar7 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; L4, L5 and L6 are selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms; The substituents in L4, L5, L6, Ar4, Ar6 and Ar7 are the same or different and are independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, alkylthio group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms or cycloalkyl group having 3 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring; R5, R6, R7 and R8 are each independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms or cycloalkyl having 3 to 10 carbon atoms; n5 is selected from 0, 1, 2, 3 or 4; n6 is selected from 0, 1, 2, 3, 4, 5 or 6; n7 is selected from 0, 1, 2 or 3; n8 is selected from 0, 1, 2, 3, 4, 5, 6 or 7.
2. The organic electroluminescent device according to claim 1, wherein: In the first compound represented by Formula 1, L, L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group or a substituted or unsubstituted pyridinyl group; Optionally, the substituents in L, L1 and L2 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, pentadeuterated phenyl or phenyl.
3. The organic electroluminescent device according to claim 1, wherein: In the first compound represented by Formula 1, L1 and L2 are each independently selected from a single bond or the group consisting of the following groups: L is selected from a single bond or the following groups:
4. The organic electroluminescent device according to claim 1, wherein: In the first compound represented by Formula 1, Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted pyrene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted spirobifluorenyl group, a group represented by Formula (X-1) or a group represented by Formula (X-2); The substituents in Ar1 and Ar2 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuterophenyl, phenyl or naphthyl; Alternatively, in formula (X-1) and formula (X-2), ring A and ring T are each independently selected from a benzene ring or a naphthalene ring; Y is selected from O, S or N(Ar); Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl; The substituents in Ar, each R3 and R4 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, pentadeuterated phenyl or phenyl.
5. The organic electroluminescent device according to claim 1, wherein: In the first compound represented by Formula 1, Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted spirobifluorenyl group or the following groups: The substituents in Ar1 and Ar2 and each of R3 and R4 are the same or different and are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuterated methyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, pentadeuterated phenyl or naphthyl; n3 represents the number of R3, and n3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; n4 represents the number of R4, and n4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; Preferably, Ar3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, and the substituents in Ar3 are the same or different and are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuterated methyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, pentadeuterated phenyl or naphthyl.
6. The organic electroluminescent device according to claim 1, wherein: In the first compound represented by Formula 1, Ar1 and Ar2 are the same or different and are each independently selected from the following groups: Optionally, Ar3 is selected from the following groups:
7. The organic electroluminescent device according to claim 1, wherein: In the first compound represented by Formula 1, Each is independently selected from the following groups: Preferably, each R1 and R2 is independently selected from hydrogen, deuterium, fluorine, cyano, trimethylsilyl, trideuterated methyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, pentadeuterated phenyl or naphthyl.
8. The organic electroluminescent device according to claim 1, wherein: In the second compound represented by Formula 2, Ar4 and Ar7 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl; Optionally, the substituents in Ar4 and Ar7 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, triphenylsilyl, trideuterated methyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl.
9. The organic electroluminescent device according to claim 1, wherein: In the second compound represented by Formula 2, L4, L5 and L6 are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted anthracene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothienyl group, and a substituted or unsubstituted dibenzofuranyl group; Optionally, the substituents in L4, L5 and L6 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuterated methyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.
10. The organic electroluminescent device according to claim 1, wherein: In the second compound represented by Formula 2, Ar6 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl; Optionally, the substituents in Ar6 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, triphenylsilyl, trideuterated methyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothienyl or carbazolyl; Preferably, each R5 and R6 is independently selected from hydrogen, deuterium, fluorine, cyano, trimethylsilyl, trideuterated methyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, pentadeuterated phenyl or naphthyl.
11. The organic electroluminescent device according to claim 1, wherein: In the second compound represented by Formula 2, Ar4 and Ar7 are each independently selected from the following groups: Preferably, Ar6 is selected from the following groups:
12. The organic electroluminescent device according to claim 1, wherein: In the second compound shown in Formula 2, Ar5 is selected from the following groups:
13. The organic electroluminescent device according to claim 1, wherein: The organic light-emitting layer comprises a host material and a dopant, wherein the host material comprises the first compound and the second compound; and the mass ratio of the first compound to the second compound is 30:70 to 70:
30.
14. The organic electroluminescent device according to claim 1, wherein: The first compound is selected from the group consisting of the following compounds: Preferably, the second compound is selected from the group consisting of the following compounds:
15. An electronic device, characterized in that An organic electroluminescent device comprising any one of claims 1 to 14.
Citation Information
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