Compound, light extraction material and application thereof

Abstract

The invention discloses a compound, a light extraction material and application thereof, and belongs to the technical field of display. The chemical structural formula of the compound is as follows: # imgabs0 # m is an integer from 1 to 4; and L1 and L2 are selected from one of a single bond, an arylene group of C6-C36, and a heteroarylene group of C2-C36. R1 and R2 are selected from one of hydrogen, deuterium, alkyl of C1-C12, alkenyl of C2-C12, cycloalkyl of C3-C12, heterocycloalkyl of C2-C12, alkoxy of C1-C12, aryl of C6-C36, heteroaryl of C2-C36, Ar1, Ar2, Ar3, Ar4, Ar5 and Ar6. The compound can be used as a light extraction layer of an OLED device, so that the OLED device has high refractive index and strong stability, and the efficiency and the service life of the device are improved.

Description

Technical Field

[0001] The present application relates to the field of display technologies, and particularly to a compound, a light extraction material and their applications. Background Art

[0002] Organic Light Emission Diodes (OLED) are widely used in the fields of lighting and display. An OLED device includes a light-emitting functional layer, and a cathode and an anode laminated on both sides of the light-emitting functional layer. By applying an electric field between the cathode and the anode, electrons are injected from the cathode, holes are injected from the anode, and the electrons and holes recombine in the light-emitting functional layer to achieve OLED electroluminescence.

[0003] Due to the difference in refractive index between different media, when light is transmitted between different media, it is likely to be lost at the interface. Therefore, currently, a Capping Layer (CPL) is usually provided on the side of the cathode facing away from the light-emitting functional layer. The CPL can enable the light confined inside the OLED device to be emitted to the outside, showing a relatively high light extraction efficiency.

[0004] However, for the materials used in the currently known light extraction layers, their refractive indices need to be improved, so that the light extraction efficiency of the light extraction layers needs to be improved. Summary of the Invention

[0005] Embodiments of the present application provide a compound, a light extraction material and their applications, which can improve the light extraction efficiency, and further improve the device efficiency and lifespan. The technical solutions are as follows:

[0006] On the one hand, a compound is provided. The compound includes a biquinoline group and at least one arylamine group, and the at least one arylamine group is respectively connected to at least one of the two benzene rings of the biquinoline group. Wherein, the chemical structural formula of the compound is as follows:

[0007]

[0008] Wherein, m is an integer from 1 to 4;

[0009] L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted C6-C36 arylene group, and a substituted or unsubstituted C2-C36 heteroarylene group;

[0010] R1 and R2 are each independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C6-C36 aryl, substituted or unsubstituted C2-C36 heteroaryl, group Ar1, group Ar2, group Ar3, group Ar4, group Ar5, group Ar6;

[0011]

[0012] Z is each independently selected from C(r1) or an N atom;

[0013] r1 is each independently selected from hydrogen, deuterium, cyano, nitro, a halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0014] X1 and Y are each independently selected from an O atom, an S atom, C(r2r3) or N(r4);

[0015] r2 and r3 are each independently selected from hydrogen, deuterium, cyano, nitro, a halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0016] r4 is selected from hydrogen, deuterium, cyano, nitro, a halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0017] Ring A and ring B are each independently selected from a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted phenanthrene ring.

[0018] In some possible implementation manners, the chemical structural formula of the compound is as follows:

[0019]

[0020] M is selected from one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C6-C36 aryl, substituted or unsubstituted C2-C36 heteroaryl, group Ar1, group Ar2, group Ar3, group Ar4, group Ar5, group Ar6.

[0021] In some possible implementation manners, the chemical structural formula of the compound is as follows:

[0022]

[0023] In some possible implementation manners, R1 and R2 are each independently selected from one of group Ar1, group Ar2, group Ar3, group Ar4, group Ar5, group Ar6.

[0024] In some possible implementation manners, group Ar1 is selected from one of the following groups:

[0025]

[0026]

[0027] In some possible implementation manners, group Ar2 is selected from one of the following groups:

[0028]

[0029] In some possible implementation manners, group Ar3 is selected from one of the following groups:

[0030]

[0031]

[0032] In some possible implementation manners, group Ar4 is selected from one of the following groups:

[0033]

[0034] In some possible implementation manners, group Ar5 is selected from one of the following groups:

[0035]

[0036] In some possible implementation manners, the group Ar6 is selected from one of the groups shown as follows:

[0037]

[0038]

[0039]

[0040] On the other hand, a light extraction material is provided, and the light extraction material includes any one of the above-mentioned compounds.

[0041] In some possible implementation manners, the mass percentage of the compound is 100%.

[0042] In some possible implementation manners, the refractive index of the light extraction material in the wavelength range of 460 nm to 620 nm is greater than 1.9.

[0043] In some possible implementation manners, the glass transition temperature of the light extraction material is greater than or equal to 129 °C.

[0044] On yet another aspect, an organic electroluminescent device is provided, and the organic electroluminescent device includes an anode, a light-emitting functional layer, a cathode, and a light extraction layer that are sequentially stacked, wherein the light extraction layer uses any one of the above-mentioned light extraction materials.

[0045] In some possible implementation manners, the light-emitting functional layer includes a hole transport unit, a light-emitting functional layer, and an electron transport unit, and the hole transport unit, the light-emitting functional layer, and the electron transport unit are sequentially stacked in the direction from the anode to the cathode;

[0046] wherein, the hole transport unit includes at least one of a hole injection layer, a hole transport layer, and an electron blocking layer;

[0047] The electron transport unit includes at least one of a hole blocking layer, an electron transport layer, and an electron injection layer.

[0048] On yet another aspect, a display device is provided, and the display device includes the above-mentioned organic electroluminescent device.

[0049] The compound provided by the embodiment of the present application combines a biquinoline group and an arylamine group. The biquinoline group is a conjugated fused-ring group with a relatively high polarizability. The side chain is an arylamine group, and the arylamine group further contains groups such as an aromatic ring or a benzheterocycle, making this type of side chain have more lone pairs of electrons. Combining with the biquinoline group, it can make the molecule have a relatively large polarizability and a relatively high refractive index. Thus, when this compound is used in the light extraction layer of an organic light-emitting device, it can make the light extraction layer have a relatively high refractive index and strong stability, thereby obtaining a relatively high light extraction efficiency, and further improving the device efficiency and lifespan of the organic light-emitting device.

[0050] It should be understood that the above general description and the following detailed description are only exemplary and do not limit the present disclosure. Description of the Drawings

[0051] Figure 1 It is the mass spectrum of bromo-biquinoline provided by the embodiment of the present application. Detailed Embodiments

[0052] The technical solutions in the embodiments of the present application will be clearly and completely described below. Apparently, the described embodiments are some but not all of the embodiments of the present application. All other embodiments obtained by those of ordinary skill in the art based on the embodiments in the present application without creative efforts shall fall within the scope of protection of the present application.

[0053] The light extraction (Capping Layer, CPL) layer, when applied to an OLED, is an organic or inorganic transparent material with a relatively high refractive index and has a relatively low absorption intensity close to zero in the visible light range. Thus, the light extraction layer can enable the light restricted inside the OLED device to exit to the outside, showing a relatively high light extraction efficiency. By adding a light extraction layer to the OLED device, the external quantum efficiency of the device can be significantly improved, the loss of light inside the device can be reduced, and thus the device efficiency can be improved. At the same time, the absorption of the light extraction layer in the ultraviolet region can avoid the influence of ultraviolet rays on the device stability.

[0054] It can be seen that the light extraction layer has an important influence on the light extraction efficiency of the OLED. However, for the materials currently used in the known light extraction layers, their refractive indices need to be improved, so that the light extraction efficiency of the light extraction layer needs to be improved.

[0055] In view of the technical problems existing in the related art, the embodiment of the present invention provides a compound, which includes a biquinoline group and at least one arylamine group, and at least one arylamine group is respectively connected to at least one of the two benzene rings of the biquinoline group. Among them, the chemical structural formula of this compound is shown as follows:

[0056]

[0057] Among them, m is an integer from 1 to 4. That is to say, the number of arylamine groups in the compound can be 1, 2, 3, or 4.

[0058]

[0059] Combined with the chemical structural formula of the biquinoline group above, the nitrogen atom of the arylamine group can be connected to any one of the carbon atoms at the 1st, 2nd, or 3rd carbon positions of the benzene ring of the biquinoline group. Further, it is at least connected to the carbon atom at the 1st carbon position of the benzene ring.

[0060] In some examples, when the number of arylamine groups in the compound is 1, the nitrogen atom of the arylamine group can be connected to any one of the two benzene rings of the biquinoline group. Further, for example, the nitrogen atom of the arylamine group can be connected to the carbon atom at the 1st carbon position of any one of the two benzene rings of the biquinoline group.

[0061] In some other examples, when the number of arylamine groups in the compound is 2, one arylamine group can be connected to each of the two benzene rings of the biquinoline group. For example, both of these benzene rings are connected to the nitrogen atom of the corresponding arylamine group through the carbon atom at the 1st carbon position. Or, one of the two benzene rings of the biquinoline group can also be connected to two arylamine groups simultaneously. For example, the 1st and 3rd carbon positions of one of the benzene rings can be connected to these two arylamine groups respectively.

[0062] In still some other examples, when the number of arylamine groups in the compound is 3 or 4, one of the two benzene rings of the biquinoline group can be connected to one or two arylamine groups, and the other is connected to two arylamine groups, and the arylamine group is at least connected to the 1st carbon positions of these two benzene rings. For the case where two arylamine groups are connected to the same benzene ring simultaneously, the 1st and 3rd carbon positions of this benzene ring can be connected to these two arylamine groups respectively.

[0063] Specifically, the chemical structural formula of the arylamine group is as follows:

[0064]

[0065] Among them, L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted C6-C36 arylene group, and a substituted or unsubstituted C2-C36 heteroarylene group.

[0066] For example, the substituted or unsubstituted C6-C36 arylene group can be a subunit of the following various aryl groups: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, perylenyl, fluoranthenyl, triphenylenyl, picenyl, pyrenyl, tetracenyl, pentacenyl, fluorenyl, indenyl, acenaphthylenyl, benzofluorenyl, spirofluorene, etc. The substituted or unsubstituted C2-C36 heteroarylene group may contain heteroatoms such as O, S, N, etc., and the above-mentioned substituted or unsubstituted C2-C36 heteroarylene group can be a subunit of the following heteroaryl groups: benzofuranyl, naphthobenzofuranyl, phenanthrenobenzofuranyl, dibenzofuranyl, benzodibenzofuranyl, benzothiophenyl, naphthobenzothiophenyl, phenanthrenobenzothiophenyl, dibenzothiophenyl, benzodibenzothiophenyl, indolyl, naphthylindolyl, carbazolyl, benzocarbazolyl, benzodisulfide group, dihydroisobenzofuranyl, dihydrobenzofuranyl, dihydrobenzothiophenyl, dihydroisobenzothiophenyl, phenoxazinyl, phenothiazinyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, etc.

[0067] In some examples, L1 and L2 are each independently selected from phenylene groups.

[0068] R1 and R2 are each independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C2-C12 alkenyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted C2-C12 heterocycloalkyl groups, substituted or unsubstituted C1-C12 alkoxy groups, substituted or unsubstituted C6-C36 aryl groups, substituted or unsubstituted C2-C36 heteroaryl groups, group Ar1, group Ar2, group Ar3, group Ar4, group Ar5, group Ar6.

[0069] For example, the substituted or unsubstituted C1-C12 alkyl group can be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, n-pentyl, isopentyl, neopentyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, octyl, etc.

[0070] The substituted or unsubstituted C2-C12 alkenyl group can be vinyl, prop-1-enyl, prop-2-enyl, prop-3-enyl, but-1-enyl, but-2-enyl, but-3-enyl, but-4-enyl, 1-methylprop-1-enyl, 2-methylprop-1-enyl, 1-ethyl-vinyl-1-yl, 2-methyl-prop-3-enyl, buta-1,3-dienyl, buta-1,2-dienyl, buta-1,2-dien-4-yl, pentenyl, hexenyl, heptenyl, octenyl, etc.

[0071] The substituted or unsubstituted C3-C12 cycloalkyl group can be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, etc.

[0072] The substituted or unsubstituted C2-C12 heterocycloalkyl group refers to an alkyl skeleton containing one or more heteroatoms, which can be oxygen atoms, nitrogen atoms, sulfur atoms, etc. Some examples of the heterocycloalkyl group can be methoxymethyl, ethoxyethyl, propoxypropyl, methoxyethyl, etc.

[0073] The substituted or unsubstituted C1-C12 alkoxy group can be methoxy, ethoxy, propoxy, butoxy, pentyloxy, etc.

[0074] The substituted or unsubstituted C6-C36 aryl group can be phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, perylenyl, fluoranthenyl, triphenylenyl, picenyl, pyrenyl, tetraphenylenyl, pentaphenylenyl, fluorenyl, indenyl, acenaphthylenyl, benzofluorenyl, spirofluorenyl, etc.

[0075] The substituted or unsubstituted C2-C36 heteroaryl group can be benzofuranyl, naphthofuranyl, phenanthrofuranyl, dibenzofuranyl, benzo[2,1-b:3,4-b']difuranyl, benzothiophenyl, naphthothiophenyl, phenanthrothiophenyl, dibenzothiophenyl, benzo[2,1-b:3,4-b']dithiophenyl, indolyl, naphthylindolyl, carbazolyl, benzocarbazolyl, benzodithioetheryl, dihydroisobenzofuranyl, dihydrobenzofuranyl, dihydrobenzothiophenyl, dihydroisobenzothiophenyl, phenoxazinyl, phenothiazinyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, etc.

[0076] The general chemical formulas of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are shown as follows:

[0077]

[0078] Each Z independently selects from C(r1) or N atoms. For example, in the Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 groups, one of the multiple Z atoms can be an N atom, and the remaining Z atoms are C(r1) atoms.

[0079] Each r1 independently selects from one of hydrogen, deuterium, cyano, nitro, halogen atoms, substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C2-C12 alkenyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted C2-C12 heterocycloalkyl groups, substituted or unsubstituted C1-C12 alkoxy groups, substituted or unsubstituted C6-C30 aryl groups, and substituted or unsubstituted C2-C30 heteroaryl groups.

[0080] X1 and Y are each independently selected from an O atom, an S atom, C(r2r3), or N(r4).

[0081] r2 and r3 are each independently selected from hydrogen, deuterium, cyano, nitro, a halogen atom, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C2-C12 alkenyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C2-C12 heterocycloalkyl group, a substituted or unsubstituted C1-C12 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heteroaryl group.

[0082] r4 is selected from hydrogen, deuterium, cyano, nitro, a halogen atom, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C2-C12 alkenyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C2-C12 heterocycloalkyl group, a substituted or unsubstituted C1-C12 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heteroaryl group.

[0083] Ring A and ring B are each independently selected from a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, or a substituted or unsubstituted phenanthrene ring.

[0084] The compound provided by the embodiment of the present application combines a biquinoline group and an arylamine group. The biquinoline group is a conjugated fused-ring group with a relatively high polarizability. The side chain is an arylamine group, and the arylamine group further contains groups such as an aromatic ring or a benzheterocycle, etc., making such side chains have more lone pairs of electrons. Cooperating with the biquinoline group, the molecule can have a relatively large polarizability and a relatively high refractive index. Thus, when this compound is used in the light extraction layer of an organic electroluminescent device, the light extraction layer can have a relatively high refractive index and strong stability, thereby obtaining a relatively high light extraction efficiency, and further improving the device efficiency and lifespan of the organic electroluminescent device.

[0085] In some examples, the embodiment of the present invention provides a compound containing a monoarylamine group, which can achieve the above effects well and also has advantages such as a simple structure and convenient synthesis. The chemical structural formula of the compound containing a monoarylamine group is as follows:

[0086]

[0087] M is selected from one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C6-C36 aryl, substituted or unsubstituted C2-C36 heteroaryl, group Ar1, group Ar2, group Ar3, group Ar4, group Ar5, group Ar6. Among them, for the specific types of each group involved in the M group, reference can be made to the specific types of each group involved in the above-mentioned R1 and R2 groups, which will not be elaborated here.

[0088] In some examples, the embodiments of the present invention provide a compound containing a bisarylamine group, which can achieve the above effects well and also has advantages such as simple structure and convenient synthesis. The chemical structural formula of the compound containing a bisarylamine group is shown as follows:

[0089]

[0090] It should be noted that L1 in these two arylamine groups can be the same or different, and L2 in these two arylamine groups can be the same or different. Moreover, L1 of one of these two arylamine groups and L2 of the other can exist independently or be connected to form a substituted or unsubstituted ring.

[0091] For any of the above-mentioned compounds, L1 and L2 are each independently selected from a single bond or a phenylene group, and L1 and L2 can be the same or different. For example, both are a single bond or both are a phenylene group, or one is a single bond and the other is a phenylene group.

[0092] For any of the above-mentioned compounds, R1 and R2 are each independently selected from one of group Ar1, group Ar2, group Ar3, group Ar4, group Ar5, group Ar6 to further improve the polarizability and refractive index of the compound.

[0093] In some examples, R1 and R2 can be the same or different. For example, R1 and R2 are the same and are each selected from one of Ar1, Ar2, Ar3, Ar4, Ar5, Ar6. Or R1 and R2 are different, that is, R1 is selected from one of Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, and R2 is selected from another one of Ar1, Ar2, Ar3, Ar4, Ar5, Ar6.

[0094] In some embodiments, group Ar1 is selected from one of the following groups:

[0095]

[0096] In some embodiments, the group Ar2 is selected from one of the groups shown below:

[0097]

[0098] In some embodiments, the group Ar3 is selected from one of the groups shown below:

[0099]

[0100]

[0101] In some embodiments, the group Ar4 is selected from one of the groups shown below:

[0102]

[0103] In some embodiments, the group Ar5 is selected from one of the groups shown below:

[0104]

[0105]

[0106] In some embodiments, the group Ar6 is selected from one of the groups shown below:

[0107]

[0108]

[0109]

[0110] Combined with the above-described compound schemes, some examples of compounds E1-E24 can be as shown below:

[0111]

[0112]

[0113]

[0114]

[0115] The refractive indices and glass transition temperatures Tg of compounds E1-E24 at different wavelengths are listed in Table 1.

[0116] Table 1

[0117]

[0118]

[0119] It can be seen that the refractive indices of the above compounds are all greater than 1.9 in the wavelength range of 460 nm to 620 nm, showing excellent light refraction effects. Moreover, the glass transition temperature of the light extraction material is greater than or equal to 129 °C, showing excellent thermal stability.

[0120] The embodiment of the present application also provides a preparation method of the above-mentioned compound, and the preparation method includes:

[0121] Synthesizing an arylamine intermediate compound; reacting the arylamine intermediate compound with a halogenated biquinoline in the presence of a protective atmosphere and a catalyst to synthesize a compound.

[0122] Among them, when synthesizing the arylamine intermediate compound, appropriate monomer compounds can be selected for reaction according to the chemical structure of the arylamine intermediate compound. Among them, one of the monomer compounds can be a halogenated monomer compound, and the arylamine intermediate compound can be synthesized through a dehydrohalogenation condensation reaction.

[0123] The reaction of the arylamine intermediate compound with the halogenated biquinoline can also be a dehydrohalogenation condensation reaction, and the halogen atom in the halogenated biquinoline can be F, Cl, Br or I. For example, the halogenated biquinoline can be brominated biquinoline.

[0124] The protective atmosphere used in the reaction process can be nitrogen, and the catalyst can be a palladium catalyst. The palladium catalyst shows high selectivity, wide substrate adaptability, mild reaction conditions and high catalytic activity. By changing reaction conditions such as the ligand, reaction solvent, temperature, and base of the palladium catalyst, the activity, selectivity, etc. of the reaction can be finely regulated to meet different synthesis requirements.

[0125] On the other hand, the embodiment of the present application also provides a light extraction material, and the light extraction material includes any one of the above-mentioned compounds. The light extraction material provided by the embodiment of the present application has all the advantages of the compound.

[0126] In some examples, the mass percentage of the compound in the light extraction material is 100%.

[0127] In some examples, the light extraction material includes a compound and an additive, and the addition amount of the additive can be adaptively determined according to actual needs. For example, the mass percentage of the additive in the light extraction material can be 1% - 5%.

[0128] Among them, the additive can be selected from at least one of materials with a refractive index lower than that of the compound, a scattering agent, and a light stabilizer. For example, nano-silica, nano-titanium dioxide, nano-zinc oxide, hindered amine light stabilizer, etc.

[0129] Based on the use of the compound provided by the embodiments of the present application, the refractive index of the light extraction material is greater than 1.9 in the wavelength range of 460 nm to 620 nm, showing excellent light refraction effect. Moreover, the glass transition temperature of the light extraction material is greater than or equal to 129 °C, showing excellent thermal stability.

[0130] On the other hand, the embodiments of the present application also provide an organic electroluminescent device, wherein the organic electroluminescent device includes an anode, a light-emitting functional layer, a cathode, and a light extraction layer which are stacked in sequence, and the light extraction layer uses any one of the above-mentioned light extraction materials. The organic electroluminescent device provided by the embodiments of the present application has all the advantages of the compound, making it have a high light extraction efficiency and device stability.

[0131] For example, the light-emitting functional layer includes a hole transport unit, a light-emitting functional layer, and an electron transport unit, and the hole transport unit, the light-emitting functional layer, and the electron transport unit are stacked in sequence from the anode to the cathode. Among them, the hole transport unit includes at least one of a hole injection layer, a hole transport layer, and an electron blocking layer; the electron transport unit includes at least one of a hole blocking layer, an electron transport layer, and an electron injection layer.

[0132] In some examples (1), the hole transport unit includes a hole transport layer, wherein the anode, the hole transport layer, and the light-emitting functional layer are stacked in sequence.

[0133] In some examples (2), the hole transport unit includes a hole injection layer and a hole transport layer, wherein the anode, the hole injection layer, the hole transport layer, and the light-emitting functional layer are stacked in sequence.

[0134] In some examples (3), the hole transport unit includes a hole transport layer and an electron blocking layer, wherein the anode, the hole transport layer, the electron blocking layer, and the light-emitting functional layer are stacked in sequence.

[0135] In some examples (4), the hole transport region includes a hole transport layer, an electron blocking layer, and a hole injection layer, wherein the anode, the hole injection layer, the hole transport layer, the electron blocking layer, and the light-emitting functional layer are stacked in sequence.

[0136] In some examples (5), the electron transport region includes an electron transport layer, wherein the cathode, the electron transport layer, and the light-emitting functional layer are stacked in sequence.

[0137] In some examples (6), the electron transport region includes an electron transport layer and an electron injection layer, wherein the cathode, the electron injection layer, the electron transport layer, and the light-emitting functional layer are stacked in sequence.

[0138] In some examples (7), the electron transport region includes an electron transport layer and a hole blocking layer, wherein the cathode, the electron transport layer, the hole blocking layer, and the light-emitting functional layer are sequentially stacked.

[0139] In some examples (8), the electron transport region includes an electron transport layer, a hole blocking layer, and an electron injection layer, wherein the cathode, the electron injection layer, the electron transport layer, the hole blocking layer, and the light-emitting functional layer are sequentially stacked.

[0140] The hole transport unit, the electron transport unit, the anode, and the cathode can all adopt currently known related materials, which will not be elaborated here.

[0141] For example, the hole injection layer includes but is not limited to: inorganic oxides, p-type dopants of strong electron-withdrawing systems, and dopants of hole transport materials, such as hexacyanohexaazatriphenylene, 2,3,5,6-tetrafluoro-7,7,8,8-tetracyano-p-benzoquinodimethane (F4TCNQ), 1,2,3-tris[(cyano)(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropane, etc.

[0142] The hole transport material / electron blocking layer includes but is not limited to: aromatic amine compounds with hole transport properties, and dimethylfluorene or carbazole materials and their derivatives.

[0143] The light-emitting layer is selected according to actual light-emitting requirements. The blue light-emitting material of the blue light-emitting layer can be pyrene derivatives, anthracene derivatives, fluorene derivatives, perylene derivatives, amine derivatives, etc. The red light-emitting material of the red light-emitting layer can be iridium complexes, carbazole derivatives, triazine derivatives, etc.

[0144] The hole blocking layer / electron transport layer includes but is not limited to: aromatic heterocyclic compounds, which can be selected from but not limited to at least one of benzimidazole, triazine, pyrimidine, pyridine, pyrazine, quinoxaline, quinoline, diazole, diazaphosphole, phosphine oxide, aromatic ketone, lactam, borane compounds and their derivatives.

[0145] The electron injection layer is generally an alkali metal or a metal, such as LiF, Yb, Mg, Ca, or their compounds, etc.

[0146] On the other hand, the embodiments of the present application also provide a display device, which includes any one of the above-mentioned organic electroluminescent devices.

[0147] The display device provided by the embodiments of the present application has all the advantages of the organic electroluminescent device. Exemplarily, the display device includes but is not limited to: OLED TVs, tablet computers, in-vehicle display screens, MP3 players, smart watches, fitness trackers, virtual reality (VR) headsets, augmented reality (AR) glasses, etc.

[0148] Exemplary embodiments of the present application will be described in more detail below. Although the exemplary embodiments of the present application are described below, it should be understood that the present application can be implemented in various forms and should not be limited by the embodiments set forth herein. For those without specific technical or conditions noted in the examples, the techniques or conditions described in the literature in this field or according to the product specifications are followed. For reagents or instruments without the manufacturer noted, they are all conventional products that can be obtained through commercial purchase.

[0149] In the following examples, bromoquinoline (abbreviated as Compound A3) is involved, which is prepared by the following method:

[0150] Raw materials:

[0151]

[0152] In a 100 - milliliter round - bottom flask, raw material 1 (1eq), raw material 2 (8eq), ferrous sulfate (0.3eq), iodine (0.01eq) and sulfuric acid (0.03eq) are added, and the reaction is heated at 110 °C. After 18 hours, the reaction is completed. The cooled mixture is neutralized with NaOH, extracted with chloroform, washed with saturated brine, and then dried with Na2SO4. The crude product obtained by column chromatography is purified by silica gel chromatography, and eluted with a hexane solution of ethyl acetate with a mass concentration of 8% as the eluent. Compound A3 is recrystallized from tetrahydrofuran / methanol with a yield of 30%. Its CAS Reaction Number is 31 - 032 - CAS - 10980486. See its mass spectrum Figure 1 , and its m / z is 413.92.

[0153] Example 1

[0154] Compound E4 was synthesized in Example 1, which was prepared by the following method:

[0155]

[0156] Toluene solvent is added to the reaction flask, and then Compound A1 1.05eq and Compound A2 1eq are added in sequence. Nitrogen is flushed into the reaction flask, and the mixture is heated under reflux for 0.5 h. Sodium tert - butoxide 1.5eq, palladium acetate 0.01eq, and X - Phos 0.02eq are added. Nitrogen is charged again, and the reaction is refluxed for 10 h. After the reaction is completed, it is cooled to room temperature, extracted, and filtered through diatomaceous earth to obtain the filtrate. After concentration, it is heated, a small amount of ethanol is added, and it is left to stand at room temperature for 4 times of recrystallization. The recrystallized solid is obtained by suction filtration and dried in a vacuum drying oven for 3 h to obtain solid intermediate 1 with a yield of 80%.

[0157] The physical property characterization of intermediate 1 is as follows: the mass spectrum m / z is 412;

[0158] 1H NMR: δ 7.21 (1H, t, J = 0.5 Hz), 7.33 - 8.05 (16H, 7.39 (ddd, J = 8.9, 1.5, 0.5 Hz), 7.48 (dddd, J = 8.0, 7.5, 1.3, 0.4 Hz), 7.53 (dd, J = 6.6, 5.1 Hz), 7.55 (ddd, J = 8.3, 2.7, 0.5 Hz), 7.57 (dddd, J = 7.9, 7.5, 1.8, 0.5 Hz), 7.62 (ddd, J = 8.9, 1.6, 0.4 Hz), 7.63 (ddd, J = 8.9, 1.8, 0.5 Hz), 7.71 (ddq, J = 8.3, 2.5, 0.5 Hz), 7.77 (dddt, J = 7.9, 2.1, 1.3, 0.5 Hz), 7.78 (ddd, J = 8.9, 1.6, 0.4 Hz), 7.87 (dddq, J = 8.0, 2.5, 1.8, 0.5 Hz), 7.99 (ddd, J = 6.6, 1.8, 0.5 Hz)), 8.22 (1H, ddq, J = 2.7, 2.1, 0.5 Hz), 8.36 (1H, ddd, J = 5.1, 1.8, 0.5 Hz).

[0159]

[0160] Add toluene solvent into the reaction flask, and then add 1 eq of compound A3 and 2.1 eq of intermediate 1 in sequence. Charge nitrogen gas into the reaction flask and heat under reflux for 0.5 h. Add 1.5 eq of sodium tert - butoxide, 0.015 eq of Pd2(dba)3, and 0.02 eq of S - Phos. Charge nitrogen gas again and reflux for 10 h. After the reaction is completed, cool to room temperature, extract, and filter through diatomaceous earth to obtain the filtrate. Concentrate and heat, add a small amount of ethanol, let it stand at room temperature for recrystallization 4 times, filter by suction to obtain the recrystallized solid, dry in a vacuum drying oven for 3 h to obtain the solid, and sublime the solid to obtain compound E4 with a yield of 68%.

[0161] The molecular formula of compound E4 is C 76 H 48 N6O2, elemental content (%): C, 84.8%; H, 4.44%; N, 7.74%.

[0162] The physical property characterization of compound E4 is as follows: mass spectrometry m / z is 1076.55;

[0163] 1H NMR: δ 7.11 (2H, t, J = 0.5 Hz), 7.31 - 8.16 (38H, 7.37 (dd, J = 6.5, 5.1 Hz), 7.44 (dddd, J = 7.9, 7.4, 1.8, 0.4 Hz), 7.44 (ddd, J = 8.8, 1.5, 0.4 Hz), 7.53 (dddd, J = 8.0, 7.4, 1.8, 0.4 Hz), 7.65 (ddd, J = 8.2, 2.0, 0.5 Hz), 7.65 (ddd, J = 8.6, 1.6, 0.4 Hz), 7.72 (dd, J = 8.7, 5.1 Hz), 7.72 (dd, J = 8.6, 0.5 Hz), 7.73 (ddq, J = 8.2, 2.6, 0.5 Hz), 7.78 (ddd, J = 8.8, 1.5, 0.4 Hz), 7.87 (dddq, J = 8.0, 2.6, 1.8, 0.5 Hz), 7.89 (dddt, J = 7.9, 2.5, 1.8, 0.5 Hz), 7.99 (ddd, J = 8.6, 2.0, 0.4 Hz), 8.02 (ddd, J = 6.5, 1.8, 0.5 Hz), 8.10 (d, J = 8.6 Hz)), 8.18 - 8.46 (8H, 8.25 (ddd, J = 8.7, 1.8, 0.5 Hz), 8.27 (ddq, J = 2.5, 2.0, 0.5 Hz), 8.37 (ddd, J = 5.1, 1.8, 0.5 Hz), 8.41 (dd, J = 5.1, 1.8 Hz)).

[0164] Example 2

[0165] Compound E6 was synthesized in Example 2 and was prepared by the following method:

[0166]

[0167] Toluene solvent was added to a reaction flask, and then 1.05 eq of Compound A1 and 1 eq of Compound A4 were successively added. Nitrogen was flushed into the reaction flask, and the mixture was heated under reflux for 0.5 h. 1.5 eq of sodium tert - butoxide, 0.01 eq of palladium acetate, and 0.02 eq of X - Phos were added. Nitrogen was flushed again, and the mixture was refluxed for 10 h. After the reaction was completed, it was cooled to room temperature, extracted, and filtered through diatomaceous earth to obtain a filtrate. After concentration, it was heated, a small amount of ethanol was added, and it was allowed to stand at room temperature for recrystallization 4 times. The recrystallized solid was obtained by suction filtration and dried in a vacuum drying oven for 3 h to obtain solid intermediate 2 with a yield of 82%.

[0168] The physical property characterization of intermediate 2 is as follows: the mass spectrum m / z is 428;

[0169] 1H NMR: δ 7.32 - 7.96 (18H, 7.39 (ddd, J = 7.8, 7.1, 1.6 Hz), 7.39 (ddd, J = 8.9, 1.5, 0.5 Hz), 7.45 (ddd, J = 7.3, 7.1, 1.6 Hz), 7.48 (dddd, J = 8.0, 7.5, 1.3, 0.4 Hz), 7.55 (ddd, J = 8.3, 2.7, 0.5 Hz), 7.57 (dddd, J = 7.9, 7.5, 1.8, 0.5 Hz), 7.63 (ddd, J = 8.9, 1.8, 0.5 Hz), 7.66 (ddd, J = 7.8, 1.6, 0.4 Hz), 7.71 (ddd, J = 8.9, 1.6, 0.4 Hz), 7.71 (ddq, J = 8.3, 2.5, 0.5 Hz), 7.77 (dddt, J = 7.9, 2.1, 1.3, 0.5 Hz), 7.78 (ddd, J = 8.9, 1.5, 0.4 Hz), 7.87 (dddq, J = 8.0, 2.5, 1.8, 0.5 Hz), 7.90 (ddd, J = 7.3, 1.6, 0.4 Hz)), 8.22 (1H, ddq, J = 2.7, 2.1, 0.5 Hz).

[0170]

[0171] Add toluene solvent into the reaction flask, then add 1 eq of compound A3 and 2.1 eq of intermediate 2 in sequence. Charge nitrogen gas into the reaction flask and heat to reflux for 0.5 h. Add 1.5 eq of sodium tert-butoxide, 0.01 eq of Pd2(dba)3, and 0.02 eq of S-Phos. Charge nitrogen gas again and reflux for 10 h. After the reaction is completed, cool to room temperature, extract, and filter through diatomaceous earth to obtain the filtrate. Concentrate and heat, add a small amount of ethanol, stand at room temperature for recrystallization 4 times, filter by suction to obtain the recrystallized solid, dry in a vacuum drying oven for 3 h to obtain the solid, and sublime the solid to obtain compound E6 with a yield of 72%.

[0172] The physical property characterization of compound E6 is as follows: The mass spectrometry m / z is 1108.49, and the molecular formula is C 76 H 48 N6S2, elemental content (%): C, 82.53%; H, 4.29%; N, 7.42%.

[0173] 1H NMR: δ 7.25 - 7.96 (38H, 7.33 (ddd, J = 8.0, 7.6, 1.7 Hz), 7.42 (ddd, J = 7.7, 7.6, 1.4 Hz), 7.44 (dddd, J = 7.9, 7.4, 1.8, 0.4 Hz), 7.44 (ddd, J = 8.8, 1.5, 0.4 Hz), 7.53 (dddd, J = 8.0, 7.4, 1.8, 0.4 Hz), 7.61 (ddd, J = 8.0, 1.4, 0.4 Hz), 7.66 (ddd, J = 8.2, 2.0, 0.5 Hz), 7.72 (dd, J = 8.7, 5.1 Hz), 7.72 (dd, J = 8.6, 0.5 Hz), 7.73 (ddq, J = 8.2, 2.6, 0.5 Hz), 7.78 (ddd, J = 8.8, 1.5, 0.4 Hz), 7.79 (ddd, J = 8.5, 1.6, 0.4 Hz), 7.85 (ddd, J = 8.5, 1.9, 0.4 Hz), 7.87 (dddq, J = 8.0, 2.6, 1.8, 0.5 Hz), 7.89 (dddt, J = 7.9, 2.5, 1.8, 0.5 Hz)), 7.96 - 8.16 (4H, 8.02 (ddd, J = 7.7, 1.7, 0.4 Hz), 8.10 (d, J = 8.6 Hz)), 8.18 - 8.32 (4H, 8.25 (ddd, J = 8.7, 1.8, 0.5 Hz), 8.27 (ddq, J = 2.5, 2.0, 0.5 Hz)), 8.41 (2H, dd, J = 5.1, 1.8 Hz).

[0174] Example 3

[0175] Compound E13 was synthesized in Example 3 and was prepared by the following method:

[0176]

[0177] Toluene solvent was added to a reaction flask, and then 1.05 eq of Compound A5 and 1 eq of Compound A6 were successively added. Nitrogen was flushed into the reaction flask, and the mixture was heated under reflux for 0.5 h. 1.5 eq of sodium tert - butoxide, 0.01 eq of palladium acetate, and 0.02 eq of X - Phos were added. Nitrogen was flushed again, and the mixture was refluxed for 10 h. After the reaction was completed, it was cooled to room temperature, extracted, and filtered through diatomaceous earth to obtain a filtrate. After concentration, it was heated, a small amount of ethanol was added, and it was allowed to stand at room temperature for 4 times of recrystallization. The recrystallized solid was obtained by suction filtration and dried in a vacuum drying oven for 3 h to obtain solid intermediate 3 with a yield of 79%.

[0178] The physical property characterization of intermediate 3 is as follows: The mass spectrometry m / z is 426;

[0179] 1H NMR: δ 7.17 - 7.51 (4H, 7.25 (dddd, J = 8.1, 7.4, 1.8, 0.5 Hz), 7.35 (ddd, J = 8.3, 7.5, 1.7 Hz), 7.37 (ddd, J = 7.6, 7.5, 1.7 Hz), 7.44 (dddd, J = 8.2, 7.4, 2.5, 0.4 Hz)), 7.55 - 7.94 (8H, 7.61 (dd, J = 8.5, 1.8 Hz), 7.65 (dd, J = 1.8, 0.5 Hz), 7.73 (ddd, J = 8.3, 1.7, 0.5 Hz), 7.73 (ddd, J = 8.6, 1.7, 0.4 Hz), 7.76 (ddd, J = 8.6, 1.6, 0.4 Hz), 7.88 (ddd, J = 7.6, 1.7, 0.5 Hz)), 7.98 - 8.21 (4H, 8.05 (dddt, J = 8.2, 2.2, 1.8, 0.5 Hz), 8.06 (dq, J = 2.7, 0.5 Hz), 8.12 (dt, J = 8.5, 0.5 Hz), 8.14 (dddt, J = 8.1, 2.7, 2.5, 0.5 Hz)), 8.75 (1H, dquint, J = 2.2, 0.5 Hz).

[0180]

[0181] Add toluene solvent into the reaction flask, then add 1 eq of compound A3 and 2.1 eq of intermediate 3 in sequence. Charge nitrogen gas into the reaction flask and heat under reflux for 0.5 h. Add 1.5 eq of sodium tert-butoxide, 0.01 eq of Pd2(dba)3, and 0.02 eq of S-Phos. Charge nitrogen gas again and reflux for 10 h. After the reaction is completed, cool to room temperature, extract, and filter through diatomaceous earth to obtain the filtrate. Concentrate and then heat, add a small amount of ethanol, let it stand at room temperature for recrystallization 4 times, filter by suction to obtain the recrystallized solid, dry in a vacuum drying oven for 3 h to obtain the solid, and sublime the solid to obtain compound E13 with a yield of 77%.

[0182] The physical property characterization of compound E13 is as follows: the mass spectrometry m / z is 1104.566, and the molecular formula is C 76 H 44 N6O4, elemental content (%): C, 82.33%; H, 4.00%; N, 7.63%.

[0183] 1H NMR: δ 7.31 - 7.62 (10H, 7.38 (dddd, J = 8.1, 7.7, 1.9, 0.5 Hz), 7.39 (ddd, J = 8.3, 7.4, 1.8 Hz), 7.41 (ddd, J = 7.9, 7.4, 1.7 Hz), 7.48 (dddd, J = 8.2, 7.7, 2.1, 0.4 Hz), 7.55 (dd, J = 8.6, 5.2 Hz)), 7.63 - 8.31 (30H, 7.68 (dd, J = 1.8, 0.5 Hz), 7.75 (ddd, J = 8.4, 1.6, 0.4 Hz), 7.76 (ddd, J = 8.3, 1.7, 0.5 Hz), 7.87 (ddd, J = 8.4, 2.0, 0.4 Hz), 7.88 (dd, J = 8.6, 0.5 Hz), 7.96 (ddd, J = 7.9, 1.8, 0.5 Hz), 8.01 (dd, J = 8.5, 1.8 Hz), 8.03 (dt, J = 8.5, 0.5 Hz), 8.08 (dq, J = 2.4, 0.5 Hz), 8.10 (dddt, J = 8.2, 2.2, 1.9, 0.5 Hz), 8.18 (d, J = 8.6 Hz), 8.20 (dddt, J = 8.1, 2.4, 2.1, 0.5 Hz), 8.24 (ddd, J = 8.6, 1.8, 0.5 Hz)), 8.39 (2H, dd, J = 5.2, 1.8 Hz), 8.81 (2H, dquint, J = 2.2, 0.5 Hz).

[0184] Example 4

[0185] Compound E19 was synthesized in Example 4 and was prepared by the following method:

[0186]

[0187] Toluene solvent was added to the reaction flask, and then 1.05 eq of compound A7 and 1 eq of compound A4 were added in sequence. Nitrogen was flushed into the reaction flask and heated under reflux for 0.5 h. 1.5 eq of sodium tert-butoxide, 0.01 eq of palladium acetate, and 0.02 eq of X-Phos were added. Nitrogen was flushed again and the reaction was refluxed for 10 h. After the reaction was completed, it was cooled to room temperature, extracted, and filtered through diatomaceous earth to obtain a filtrate. After concentration, it was heated, a small amount of ethanol was added, and it was allowed to stand at room temperature for recrystallization 4 times. The recrystallized solid was obtained by suction filtration and dried in a vacuum drying oven for 3 h to obtain solid intermediate 4 with a yield of 45%.

[0188] The physical property characterization of intermediate 4 is as follows: The mass spectrum m / z is 467;

[0189] 1H NMR: δ 7.30 - 8.02 (20H, 7.38 (ddd, J = 7.8, 7.1, 1.6 Hz), 7.42 (ddd, J = 7.3, 7.1, 1.4 Hz), 7.43 (dd, J = 1.8, 0.4 Hz), 7.44 (dt, J = 8.6, 0.4 Hz), 7.45 (ddd, J = 8.1, 6.4, 1.8 Hz), 7.46 (tdd, J = 7.8, 1.8, 1.1 Hz), 7.47 (ddd, J = 7.7, 6.4, 1.7 Hz), 7.57 (dddd, J = 8.1, 7.8, 1.6, 0.4 Hz), 7.67 (dd, J = 8.6, 1.8 Hz), 7.69 (ddd, J = 8.9, 1.6, 0.4 Hz), 7.75 (ddd, J = 8.9, 1.6, 0.4 Hz), 7.82 (ddt, J = 8.1, 1.7, 0.4 Hz), 7.84 (ddd, J = 7.8, 1.4, 0.4 Hz), 7.89 (ddd, J = 7.3, 1.6, 0.4 Hz), 7.94 (dddd, J = 8.1, 1.5, 1.3, 0.4 Hz), 7.95 (ddd, J = 7.7, 1.8, 0.4 Hz)).

[0190]

[0191] Add toluene solvent into the reaction flask, then add 1 eq of compound A3 and 2.1 eq of intermediate 4 in sequence. Charge nitrogen gas into the reaction flask and heat under reflux for 0.5 h. Add 1.5 eq of sodium tert - butoxide, 0.01 eq of Pd2(dba)3, and 0.02 eq of S - Phos. Charge nitrogen gas again and reflux for 10 h. After the reaction is completed, cool to room temperature, extract, and filter through diatomaceous earth to obtain the filtrate. Concentrate and heat, add a small amount of ethanol, let it stand at room temperature for recrystallization 4 times, filter by suction to obtain the recrystallized solid, dry it in a vacuum drying oven for 3 h to obtain the solid, and sublime the solid to obtain compound E19 with a yield of 69%.

[0192] The physical property characterization of compound E19 is as follows: The mass spectrometry m / z is 1186.336, and the molecular formula is C 80 H 50 N8S2, elemental content (%): C, 80.940%; H, 4.243%; N, 9.439%.

[0193] 1H NMR: δ 7.06 (2H, dt, J = 8.5, 0.4 Hz), 7.26 - 8.09 (42H, 7.33 (ddd, J = 7.6, 6.0, 2.6 Hz), 7.35 (ddd, J = 7.7, 7.2, 1.7 Hz), 7.39 (ddd, J = 8.0, 7.2, 1.7 Hz), 7.44 (tdd, J = 7.6, 1.9, 1.1 Hz), 7.52 (ddd, J = 8.1, 6.0, 1.6 Hz), 7.54 (dddd, J = 8.0, 7.6, 1.6, 0.4 Hz), 7.54 (dd, J = 8.6, 5.2 Hz), 7.55 (dd, J = 1.8, 0.5 Hz), 7.65 (ddd, J = 8.0, 1.7, 0.4 Hz), 7.74 (ddd, J = 8.5, 1.6, 0.4 Hz), 7.76 (dd, J = 8.6, 0.5 Hz), 7.85 (ddd, J = 7.6, 1.6, 0.4 Hz), 7.89 (dd, J = 8.5, 1.8 Hz), 7.93 (dddd, J = 8.0, 1.5, 1.2, 0.4 Hz), 7.99 (ddd, J = 8.5, 2.0, 0.4 Hz), 8.02 (ddt, J = 8.1, 2.6, 0.4 Hz), 8.03 (ddd, J = 7.7, 1.7, 0.4 Hz)), 8.11 - 8.30 (4H, 8.17 (d, J = 8.6 Hz), 8.24 (ddd, J = 8.6, 1.8, 0.5 Hz)), 8.39 (2H, dd, J = 5.2, 1.8 Hz).

[0194] Example 5

[0195] Compound E23 was synthesized in Example 5 and was prepared by the following method:

[0196]

[0197] Toluene solvent was added to a reaction flask, and then 1.05 eq of Compound A8 and 1 eq of Compound A2 were successively added. Nitrogen was flushed into the reaction flask and heated under reflux for 0.5 h. 1.5 eq of sodium tert - butoxide, 0.01 eq of palladium acetate, and 0.02 eq of X - Phos were added. Nitrogen was filled again, and the reaction was refluxed for 10 h. After the reaction was completed, it was cooled to room temperature, extracted, and filtered through diatomaceous earth to obtain a filtrate. After concentration, it was heated, a small amount of ethanol was added, and it was allowed to stand at room temperature for 4 times of recrystallization. The recrystallized solid was obtained by suction filtration and dried in a vacuum drying oven for 3 h to obtain solid intermediate 5 with a yield of 63%.

[0198] The physical property characterization of intermediate 5 is as follows: The mass spectrum m / z is 403;

[0199] 1H NMR δ 7.13 (2H, t, J = 0.5 Hz), 7.42 (2H, dd, J = 6.5, 5.1 Hz), 7.58 - 7.81 (8H, 7.64 (ddd, J = 8.8, 1.6, 0.4 Hz), 7.74 (ddd, J = 8.8, 1.8, 0.4 Hz)), 8.00 (2H, ddd, J = 6.5, 1.8, 0.5 Hz), 8.37 (2H, ddd, J = 5.1, 1.8, 0.5 Hz).

[0200]

[0201] Add toluene solvent into the reaction flask, and then successively add 1.05 eq of compound A3 and 1 eq of compound A9. Charge nitrogen gas into the reaction flask and heat under reflux for 0.5 h. Add 1.5 eq of sodium tert-butoxide, 0.01 eq of palladium acetate, and 0.02 eq of X-Phos. Charge nitrogen gas again and reflux for 10 h. After the reaction is completed, cool to room temperature, extract, and filter through diatomaceous earth to obtain the filtrate. Concentrate and heat, add a small amount of ethanol, stand at room temperature for recrystallization 4 times, filter by suction to obtain the recrystallized solid, and dry in a vacuum drying oven for 3 h to obtain solid intermediate 6 with a yield of 83%.

[0202] The physical property characterization of intermediate 6 is as follows: The mass spectrometry m / z is 410;

[0203] 1H NMR: δ 7.35 (1H, dd, J = 8.7, 5.1 Hz), 7.53 (1H, tdd, J = 7.7, 1.6, 1.4 Hz), 7.59 - 7.92 (7H, 7.65 (dd, J = 8.6, 0.5 Hz), 7.69 (dddd, J = 8.0, 7.7, 1.5, 0.5 Hz), 7.69 (dd, J = 7.5, 5.2 Hz), 7.80 (dd, J = 8.7, 0.5 Hz), 7.86 (dtd, J = 8.0, 1.5, 0.5 Hz)), 8.21 - 8.36 (3H, 8.27 (d, J = 8.7 Hz), 8.30 (ddd, J = 7.5, 1.9, 0.5 Hz), 8.30 (d, J = 8.6 Hz)), 8.45 - 8.61 (3H, 8.51 (dd, J = 5.1, 1.7 Hz), 8.53 (ddd, J = 8.7, 1.7, 0.5 Hz), 8.55 (dd, J = 5.2, 1.9 Hz)).

[0204]

[0205] Add toluene solvent into the reaction flask, and then add 1.05eq of intermediate 5 and 1eq of intermediate 6 in sequence. Charge nitrogen into the reaction flask and heat to reflux for 0.5h. Add 1.5eq of sodium tert-butoxide, 0.01eq of Pd2(dba)3, and 0.02eq of S-Phos. Charge nitrogen again and reflux for 10h. After the reaction is completed, cool to room temperature, extract, and filter through diatomaceous earth to obtain the filtrate. Concentrate and heat, add a small amount of ethanol, let it stand at room temperature for recrystallization 4 times, filter by suction to obtain the recrystallized solid, dry it in a vacuum drying oven for 3h to obtain the solid, and obtain compound E23 after sublimation, with a yield of 63%.

[0206] The physical property characterization of compound E23 is as follows: the mass spectrum m / z is 733.242, and the element content (%): C50H31N5O2, C, 81.835; H, 4.253; N, 9.545.

[0207] 1H NMR: δ7.03 - 7.17(3H, 7.10(dd, J = 8.6, 5.1Hz), 7.12(t, J = 0.5Hz)), 7.32(2H, dd, J = 6.9, 5.1Hz), 7.45 - 7.74(9H, 7.52(tdd, J = 7.7, 1.6, 1.4Hz), 7.53(dd, J = 6.1, 5.2Hz), 7.58(dd, J = 8.6, 0.5Hz), 7.65(ddd, J = 8.6, 1.6, 0.4Hz), 7.67(dddd, J = 7.9, 7.7, 1.5, 0.5Hz)), 7.75 - 7.93(7H, 7.81(dd, J = 8.7, 0.5Hz), 7.84(dtd, J = 7.9, 1.5, 0.5Hz), 7.86(ddd, J = 8.6, 2.0, 0.4Hz)), 8.02(2H, ddd, J = 6.9, 1.8, 0.4Hz), 8.19 - 8.44(5H, 8.25(d, J = 8.7Hz), 8.28(ddd, J = 6.1, 1.9, 0.5Hz), 8.36(d, J = 8.6Hz), 8.38(ddd, J = 5.1, 1.8, 0.5Hz)), 8.45 - 8.60(3H, 8.51(dd, J = 5.1, 1.8Hz), 8.52(ddd, J = 8.6, 1.8, 0.5Hz), 8.54(dd, J = 5.2, 1.9Hz)).

[0208] Example 6

[0209] Compound E24 was synthesized in Example 6 and was prepared by the following method:

[0210]

[0211] Add toluene solvent into the reaction flask, and then successively add 1.05 eq of compound A10 and 1 eq of compound A6. Charge nitrogen into the reaction flask and heat under reflux for 0.5 h. Add 1.5 eq of sodium tert-butoxide, 0.01 eq of palladium acetate, and 0.02 eq of X-Phos. Charge nitrogen again and reflux for 10 h. After the reaction is completed, cool to room temperature, extract, and filter through diatomaceous earth to obtain the filtrate. Concentrate and heat, add a small amount of ethanol, let it stand at room temperature and recrystallize 4 times, filter by suction to obtain the recrystallized solid, and dry it in a vacuum drying oven for 3 h to obtain solid intermediate 7 with a yield of 85%.

[0212] The physical property characterization of intermediate 7 is as follows: the mass spectrum m / z is 403, and the molecular formula is C 26 H 17 N3O2, elemental content (%) : C, 77.42%; H, 4.253%.

[0213] 1H NMR: δ7.28 - 7.44(4H, 7.35(ddd, J = 8.1, 7.5, 1.6Hz), 7.37(ddd, J = 7.6, 7.5, 1.7Hz)), 7.67 - 7.80(10H, 7.73(ddd, J = 8.5, 1.5, 0.4Hz), 7.73(ddd, J = 8.5, 1.7, 0.4Hz), 7.74(ddd, J = 8.1, 1.7, 0.5Hz)), 7.90(2H, ddd, J = 7.6, 1.6, 0.5Hz).

[0214]

[0215] Add toluene solvent into the reaction flask, and then successively add 1 eq of intermediate 7 and 1.1 eq of intermediate 6 involved above. Charge nitrogen into the reaction flask and heat under reflux for 0.5 h. Add 1.5 eq of sodium tert-butoxide, 0.01 eq of Pd2(dba)3, and 0.02 eq of S-Phos. Charge nitrogen again and reflux for 10 h. After the reaction is completed, cool to room temperature, extract, and filter through diatomaceous earth to obtain the filtrate. Concentrate and heat, add a small amount of ethanol, let it stand at room temperature and recrystallize 4 times, filter by suction to obtain the recrystallized solid, and dry it in a vacuum drying oven for 3 h to obtain the solid. After sublimation of the solid, compound E24 is obtained with a yield of 64%.

[0216] The physical property characterization of compound E24 is as follows: the mass spectrum m / z is 733.25, and the molecular formula is C 50 H 31 N5O2, elemental content (%) : C, 81.84%; H, 4.253%; N, 9.533%.

[0217] 1H NMR: δ 7.10 (1H, dd, J = 8.6, 5.1 Hz), 7.30 - 7.45 (4H, 7.38 (ddd, J = 8.3, 7.4, 1.8 Hz), 7.38 (ddd, J = 7.9, 7.4, 1.6 Hz)), 7.45 - 8.03 (20H, 7.52 (tdd, J = 7.7, 1.6, 1.4 Hz), 7.53 (dd, J = 6.1, 5.2 Hz), 7.58 (dd, J = 8.6, 0.5 Hz), 7.67 (dddd, J = 7.9, 7.7, 1.5, 0.5 Hz), 7.75 (ddd, J = 8.4, 1.6, 0.4 Hz), 7.75 (ddd, J = 8.3, 1.6, 0.5 Hz), 7.81 (dd, J = 8.7, 0.5 Hz), 7.84 (dtd, J = 7.9, 1.5, 0.5 Hz), 7.89 (ddd, J = 8.4, 2.0, 0.4 Hz), 7.96 (ddd, J = 7.9, 1.8, 0.5 Hz)), 8.19 - 8.42 (3H, 8.25 (d, J = 8.7 Hz), 8.28 (ddd, J = 6.1, 1.9, 0.5 Hz), 8.36 (d, J = 8.6 Hz)), 8.45 - 8.60 (3H, 8.51 (dd, J = 5.1, 1.8 Hz), 8.52 (ddd, J = 8.6, 1.8, 0.5 Hz), 8.54 (dd, J = 5.2, 1.9 Hz)).

[0218] Comparative Example

[0219] Comparative Example 1 involves compound Ref1, Comparative Example 2 involves compound Ref2, and Comparative Example 3 involves compound Ref3. Their chemical structural formulas are shown as follows:

[0220]

[0221] The refractive indices and glass transition temperatures of compound Ref1, compound Ref2, and compound Ref3 at different wavelengths are listed in Table 2.

[0222] Table 2

[0223]

[0224] It can be seen that the refractive indices of the compounds provided in the examples of the present invention are all improved compared with compound Ref1, compound Ref2, and compound Ref3. When used as a light extraction layer material, this is beneficial to improving the light extraction efficiency of OLEDs, obtaining a higher external quantum efficiency, reducing the loss of light inside the device, and thus improving the device efficiency.

[0225] Test Example 1

[0226] The compounds provided in the above Examples 1 - 4 and the compounds Ref1 - Ref3 provided in Comparative Examples 1 - 3 were used as the light extraction layer, and multiple OLED devices were respectively provided.

[0227] The OLED device is a top - emitting device prepared by vacuum evaporation, which includes an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light - emitting layer (including a host and a guest dopant), a hole blocking layer, an electron transport layer, an electron injection layer, a cathode, and a light extraction layer arranged in layers in sequence.

[0228] Among them, the materials involved in each layer of the OLED device are as follows:

[0229]

[0230]

[0231] (1) The structure and layer thickness of the blue - light OLED device are as follows. Among them, the percentages involved in the following layers are the mass percentages of the current materials in the total mass of the layer:

[0232] ITO / m - MTDATA + 3% F4TCNQ 10nm / m - MTDATA 110nm / CBP 5nm / BH + 5% of BD 20nm / TPBi 5nm / BCP:Liq(1:1) 30nm / Yb 1nm / Mg:Ag 13nm / CPL 65nm.

[0233] Performance tests were carried out on this blue - light OLED device, and the test results are shown in Table 3.

[0234] Table 3

[0235]

[0236] As can be seen from Table 3, compared with the compounds Ref1 - Ref3, the blue - light OLED device prepared by using the compounds provided in the embodiments of the present application as the light extraction layer has a higher light extraction efficiency, a certain improvement in stability, and obvious improvements in both efficiency and lifespan.

[0237] (2) The structure and layer thickness of the green - light OLED device are as follows. Among them, the percentages involved in the following layers are the mass percentages of the current materials in the total mass of the layer:

[0238] ITO / m - MTDATA + 3% F4TCNQ 10nm / m - MTDATA 110nm / CBP 5nm / GH + 10% of GD 40nm / TPBi 5nm / BCP:Liq(1:1) 30nm / Yb 1nm / Mg:Ag 13nm / CPL 65nm.

[0239] Performance tests were conducted on the green OLED device, and the test results are shown in Table 4.

[0240] Table 4

[0241]

[0242] As can be seen from Table 4, compared with compounds Ref1-Ref3, the green OLED device prepared by using the compound provided in the embodiment of the present application as the light extraction layer has higher light extraction efficiency, certain improvement in stability, and obvious improvement in both efficiency and lifespan.

[0243] (3) The structure and layer thickness of the red OLED device are as follows. Among them, the percentages involved in the following layers are the mass percentages of the current materials in the total mass of the layer:

[0244] ITO / m-MTDATA + 3% F4TCNQ 10nm / m-MTDATA 110nm / CBP 5nm / RH + 3% D of RD 45nm / TPBi 5nm / BCP:Liq(1:1) 30nm / Yb 1nm / Mg:Ag 13nm / CPL 65nm.

[0245] Performance tests were conducted on the red OLED device, and the test results are shown in Table 5.

[0246] Table 5

[0247]

[0248] As can be seen from Table 5, compared with compounds Ref1-Ref3, the red OLED device prepared by using the compound provided in the embodiment of the present application as the light extraction layer has higher light extraction efficiency, certain improvement in stability, and obvious improvement in both efficiency and lifespan.

[0249] The above description is only for the convenience of those skilled in the art to understand the technical solution of the present application, and is not intended to limit the present application. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present application shall be included within the protection scope of the present application.

Claims

1. A compound, characterized in that, The compound includes a biquinoline group and at least one arylamine group, and the at least one arylamine group is respectively connected to at least one of the two benzene rings of the biquinoline group. The chemical structural formula of the compound is as follows: Wherein, m is an integer from 1 to 4; L1 and L2 each independently selected from a single bond, a substituted or unsubstituted C6-C36 arylene, a substituted or unsubstituted C2-C36 heteroarylene; R1 and R2 each independently selected from hydrogen, deuterium, a substituted or unsubstituted C1-C12 alkyl, a substituted or unsubstituted C2-C12 alkenyl, a substituted or unsubstituted C3-C12 cycloalkyl, a substituted or unsubstituted C2-C12 heterocycloalkyl, a substituted or unsubstituted C1-C12 alkoxy, a substituted or unsubstituted C6-C36 aryl, a substituted or unsubstituted C2-C36 heteroaryl, group Ar1, group Ar2, group Ar3, group Ar4, group Ar5, group Ar6; Z each independently selected from C(r1) or N atom; r1 each independently selected from hydrogen, deuterium, cyano, nitro, halogen atom, a substituted or unsubstituted C1-C12 alkyl, a substituted or unsubstituted C2-C12 alkenyl, a substituted or unsubstituted C3-C12 cycloalkyl, a substituted or unsubstituted C2-C12 heterocycloalkyl, a substituted or unsubstituted C1-C12 alkoxy, a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted C2-C30 heteroaryl; X1, Y each independently selected from O atom, S atom, C(r2r3) or N(r4); r2, r3 each independently selected from hydrogen, deuterium, cyano, nitro, halogen atom, a substituted or unsubstituted C1-C12 alkyl, a substituted or unsubstituted C2-C12 alkenyl, a substituted or unsubstituted C3-C12 cycloalkyl, a substituted or unsubstituted C2-C12 heterocycloalkyl, a substituted or unsubstituted C1-C12 alkoxy, a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted C2-C30 heteroaryl; r4 selected from hydrogen, deuterium, cyano, nitro, halogen atom, a substituted or unsubstituted C1-C12 alkyl, a substituted or unsubstituted C2-C12 alkenyl, a substituted or unsubstituted C3-C12 cycloalkyl, a substituted or unsubstituted C2-C12 heterocycloalkyl, a substituted or unsubstituted C1-C12 alkoxy, a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted C2-C30 heteroaryl; Ring A and ring B each independently selected from a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted phenanthrene ring.

2. The compound according to claim 1, characterized in that, The chemical structural formula of the compound is as follows: M is selected from one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C6-C36 aryl, substituted or unsubstituted C2-C36 heteroaryl, group Ar1, group Ar2, group Ar3, group Ar4, group Ar5, group Ar6.

3. The compound according to claim 1, wherein The chemical structural formula of the said compound is as follows:

4. The compound according to any one of claims 1-3, characterized in that, R1 and R2 are each independently selected from one of group Ar1, group Ar2, group Ar3, group Ar4, group Ar5, group Ar6.

5. The compound according to claim 4, wherein The said group Ar1 is selected from one of the following groups:

6. The compound according to claim 4, wherein The said group Ar2 is selected from one of the following groups:

7. The compound according to claim 4, wherein The said group Ar3 is selected from one of the following groups:

8. The compound according to claim 4, characterized in that, The said group Ar4 is selected from one of the following groups:

9. The compound according to claim 4, characterized in that, The said group Ar5 is selected from one of the following groups:

10. The compound according to claim 4, characterized in that, The said group Ar6 is selected from one of the following groups:

11. A light extraction material, characterized in that, The said light extraction material comprises the compound according to any one of claims 1 to 10.

12. The light extraction material according to claim 11, wherein The mass percentage of the said compound is 100%.

13. The light extraction material according to any one of claims 11 to 12, characterized in that, The refractive index of the said light extraction material is greater than 1.9 in the wavelength range of 460nm to 620nm.

14. The light extraction material according to any one of claims 11 to 13, characterized in that, The glass transition temperature of the said light extraction material is greater than or equal to 129°C.

15. An organic electroluminescent device, characterized in that, The said organic electroluminescent device comprises an anode, a light-emitting functional layer, a cathode and a light extraction layer which are stacked in sequence, wherein the said light extraction layer uses the light extraction material according to any one of claims 11 to 14.

16. The organic electroluminescent device according to claim 15, wherein The said light-emitting functional layer comprises a hole transport unit, a light-emitting functional layer and an electron transport unit, and the said hole transport unit, the said light-emitting functional layer and the said electron transport unit are stacked in sequence from the anode to the cathode; Wherein, the said hole transport unit comprises at least one of a hole injection layer, a hole transport layer, an electron blocking layer; The said electron transport unit comprises at least one of a hole blocking layer, an electron transport layer, an electron injection layer.

17. A display device, characterized in that, The said display device comprises the organic electroluminescent device according to any one of claims 15 to 16.

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