Spirofluorene organic compound, organic light-emitting ink material and application of spirofluorene organic compound

Abstract

The invention relates to a spirofluorene organic compound, an organic light-emitting ink material and application thereof. The spirofluorene organic compound has the structural characteristics as shown in the following formula I. The spirofluorene organic compound has good dissolvability and film-forming property, is suitable for a solution processing technology of a device, and can improve the efficiency and stability of the device. # imgabs0 #

Description

Technical Field

[0001] The present application relates to the field of organic electroluminescence technology, and particularly to a spirofluorene-based organic compound, an organic light-emitting ink material and their applications. Background Art

[0002] Organic optoelectronic materials are a class of organic materials with properties such as the generation, conversion, and transmission of photons and electrons. At present, the controllable optoelectronic properties of organic optoelectronic materials have been applied to organic light-emitting diodes (OLEDs), organic solar cells (OPVs), organic field effect transistors (OFETs), and even organic lasers. In recent years, OLEDs have become a very popular new type of flat panel display product at home and abroad. OLED displays have the characteristics of self-luminescence, wide viewing angle, short response time, high luminous efficiency, wide color gamut, low operating voltage, thin panel, large-size flexible panel fabrication, and low cost, and are hailed as the star flat panel display products of the 21st century.

[0003] Regarding the history of organic electroluminescence, it can be traced back to the report by Bernanose et al. in 1953. Approximately 10 years later, in 1963, Pope et al. at New York University applied a voltage to a crystal of anthracene and observed the fluorescence emission of anthracene. In 1987, C.W. Tang et al. of Kodak Company in the United States used ultra-thin film technology, using an aromatic amine with good hole transport effect as the hole transport layer, an aluminum complex of 8-hydroxyquinoline as the light-emitting layer, indium tin oxide (ITO) film and metal alloy as the anode and cathode respectively, to prepare a light-emitting device, and the device obtained a brightness of up to 1000 cd / m at a driving voltage of 10V. 2With the green light emission and an efficiency of 1.5 lm / W for the device, this breakthrough has enabled the rapid and in-depth development of organic electroluminescence research worldwide. In 1990, Burroughes et al. from the University of Cambridge proposed the first polymer (PPV)-based light-emitting diode, indicating that PPV can serve as a highly fluorescent emission material in a single-layer device with relatively high luminescence efficiency. In 1998, Baldo, Forrest et al. from Princeton University reported the first phosphorescent device based on electroluminescence, which can in principle have an internal quantum yield of 100%. However, on the one hand, phosphorescent materials generally use precious metals such as iridium and platinum, which are expensive. On the other hand, for deep blue phosphorescent materials, there are still problems such as chemical instability and significant efficiency roll-off at high current densities in the device. Therefore, it is extremely important to develop an OLED device that uses inexpensive and stable organic small molecule materials and can achieve high-efficiency light emission.

[0004] In 2012, the research group of Adachi at Kyushu University reported a highly efficient all-fluorescent OLED device based on the thermally activated delayed fluorescence (TADF) mechanism. When the energy level difference between the S1 and T1 of the molecule is small enough, triplet excitons can absorb thermal energy and return to the singlet state through the RISC process, and then emit fluorescence. The internal quantum efficiency (IQE) of its device can theoretically reach 100%, and the external quantum efficiency (EQE) can even be as high as 30%, comparable to the level of phosphorescent devices. Therefore, the research on TADF materials as the next-generation luminescent materials is in full swing.

[0005] TADF molecules are mainly doped as guest materials in wide-bandgap host materials to achieve highly efficient thermally activated delayed fluorescence. Different from the emission of traditional fluorescent molecules from the local (LE) state, TADF emission mainly originates from the transition of the ICT state, so it is easily affected by the vibrational and rotational motions between the donor and acceptor, resulting in low electroluminescence efficiency and poor stability. Therefore, it is very necessary to research and develop highly efficient and highly stable TADF materials.

[0006] There is a method to provide TADF materials based on the boron-nitrogen resonance framework, which have high efficiency and narrow-band emission characteristics. However, their solubility and film-forming properties are poor. Therefore, most of the reported compounds of this type are evaporation-type materials, which are difficult to be applied to the solution processing technology of OLEDs with lower cost and more convenient for popularization and application. Summary of the Invention

[0007] Based on this, the present application provides a spirofluorene-based organic compound, an organic light-emitting ink material and their applications. The spirofluorene-based organic compound has good solubility and film-forming properties, is suitable for the solution processing technology of devices, and can simultaneously improve the efficiency and stability of the devices.

[0008] In the first aspect of the present application, a spirofluorene-based organic compound is provided, which has the structural characteristics shown in the following formula I:

[0009]

[0010] Wherein, Q is a boron-nitrogen doped polycyclic aryl group, n is 1 or 2, represents a single bond or non-bonding.

[0011] In the second aspect of the present application, an organic light-emitting composition is provided, which includes a light-emitting material and a host material. The light-emitting material includes one or more of the spirofluorene-based organic compounds described in the first aspect;

[0012] The host material includes a first host material and a second host material. The first host material is a compound containing a carbazole group, and the second host material is one or more of a dicyanobenzene-based compound and a phosphorescent compound containing metal Ir.

[0013] In the third aspect of the present application, an organic light-emitting ink material is provided, which includes one or more of the spirofluorene-based organic compounds described in the first aspect and the organic light-emitting composition described in the second aspect, and a solvent system.

[0014] In the fourth aspect of the present application, an organic electronic device is provided, which includes a functional layer. The functional layer contains one or more of the spirofluorene-based organic compounds described in the first aspect and the organic light-emitting composition described in the second aspect, or the functional layer is prepared from the organic light-emitting ink material described in the third aspect.

[0015] In the fifth aspect of the present application, a display device or a lighting device is provided, which includes the organic electroluminescent device described in the fourth aspect.

[0016] The above spirofluorene-based organic compound, by introducing a spirofluorene-based group on the basis of a boron-nitrogen doped polycyclic aryl group, has good solubility and film-forming property, is suitable for the solution processing technology of devices, is beneficial to reducing the production cost of organic electronic devices, and is convenient for its popularization and application. Further, the spirofluorene-based organic compound and the host material together as an organic light-emitting material can improve the efficiency and stability of the device. Description of the Drawings

[0017] Figure 1 It is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application. Among them, 1 is an ITO anode, 2 is a first hole transport layer, 3 is a second hole transport layer, 4 is a light-emitting layer, 5 is a first electron transport layer, 6 is a second electron transport layer, 7 is an electron injection layer, and 8 is a metal cathode.

[0018] Figure 2is the electroluminescence spectrum of Device 2, with its emission peak located at 519 nm and a full width at half maximum of 37 nm.

[0019] Figure 3 is the electroluminescence spectrum of Device 5, with its emission peak located at 528 nm and a full width at half maximum of 45 nm. Specific Embodiments

[0020] The following further describes in detail the spirofluorene-based organic compounds, organic light-emitting ink materials and their applications of the present application in combination with specific embodiments. The present application can be implemented in many different forms and is not limited to the embodiments described herein. On the contrary, these embodiments are provided to make the understanding of the disclosed content of the present application more thorough and comprehensive.

[0021] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the technical field to which this application belongs. The terms used in the description of the present application herein are only for the purpose of describing specific embodiments and are not intended to limit this application.

[0022] As used herein, "one or more" refers to any one, any two, or any two or more of the listed items.

[0023] In the present application, "the first aspect", "the second aspect", "the third aspect", "the fourth aspect", etc. are only for descriptive purposes and should not be construed as indicating or implying relative importance or quantity, nor should they be construed as implicitly indicating the importance or quantity of the indicated technical features. Moreover, "the first", "the second", "the third", "the fourth", etc. only serve the purpose of non-exhaustive enumerative description and should be understood not to constitute a closed limitation on quantity.

[0024] In the present application, among the technical features described in an open-ended manner, there are included closed technical solutions composed of the listed features, as well as open technical solutions including the listed features.

[0025] In the present application, when it comes to numerical ranges, unless otherwise specified, the above numerical ranges are considered continuous and include the minimum and maximum values of the range, as well as each value between such minimum and maximum values. Further, when the range refers to integers, it includes each integer between the minimum and maximum values of the range. In addition, when multiple ranges are provided to describe features or characteristics, these ranges can be combined. In other words, unless otherwise specified, all ranges disclosed herein should be understood to include any and all sub-ranges subsumed therein.

[0026] In the present application, for the percentage content involved, unless otherwise specified, for solid-liquid mixtures and solid-solid mixtures, it refers to the mass percentage, and for liquid-liquid mixtures, it refers to the volume percentage.

[0027] In this application, unless otherwise specified, the percentage concentration refers to the final concentration. The final concentration refers to the proportion of the added component in the system after adding the component.

[0028] In this application, unless otherwise specified, the temperature parameter allows both constant temperature treatment and treatment within a certain temperature range. The constant temperature treatment allows the temperature to fluctuate within the accuracy range controlled by the instrument.

[0029] Room temperature in this application generally refers to 4°C to 30°C, preferably 20 ± 5°C.

[0030] In this application, those skilled in the art can select groups and their substituents to provide stable structural moieties and compounds. When a substituent is described by a chemical formula written from left to right, the substituent also includes the chemically equivalent substituent obtained when writing the structural formula from right to left.

[0031] The chapter headings used in this application are only for the purpose of organizing the article and should not be construed as limiting the subject matter. All documents or portions of documents cited in this invention, including but not limited to patents, patent applications, articles, books, operating manuals, and theses, are hereby incorporated by reference in their entirety.

[0032] Unless otherwise specified, all technical and scientific terms used in this application have the standard meanings in the field to which the claimed subject matter pertains. If there are multiple definitions for a term, the definition in this article shall prevail.

[0033] It should be understood that the singular forms used in this application, such as "a", include plural referents unless otherwise specified. In addition, the term "comprising" is an open-ended limitation and not a closed one, that is, it includes the content specified in the present invention but does not exclude other aspects.

[0034] Unless otherwise stated, this application adopts the traditional methods of mass spectrometry and elemental analysis, and the steps and conditions can refer to the conventional operating steps and conditions in the art.

[0035] Unless otherwise specified, this application adopts the standard nomenclature and standard laboratory procedures and techniques of analytical chemistry, organic synthetic chemistry, and optics. In some cases, standard techniques are used for chemical synthesis, chemical analysis, and detection of the performance of light-emitting devices.

[0036] The compounds of this application may contain non-natural proportions of atomic isotopes on one or more atoms constituting the compound. For example, the compound can be labeled with a radioactive isotope, such as deuterium (2H). All transformations of the isotope composition of the compounds of this application, whether radioactive or not, are included within the scope of this application.

[0037] In this application, unless otherwise specified, the number of "substitutions" may be one or more; when there are multiple ones, it means more than two, for example, it may be 2, 3, or 4. And when the number of "substitutions" is multiple, the "substitutions" may be the same or different. In this application, the position of "substitution", unless otherwise specified, can be arbitrary.

[0038] In this application, as a group or part of other groups (such as in groups like halogen-substituted alkyl), the term "alkyl" means a saturated aliphatic hydrocarbon group including branched and straight-chain ones with a specified number of carbon atoms. For example, C1-C20 alkyl includes straight-chain or branched alkyl groups with 1-20 carbon atoms. As defined in "C1-C6 alkyl", it includes groups with 1, 2, 3, 4, 5, or 6 carbon atoms in a straight-chain or branched structure. For example, in this application, the C1-C6 alkyls are each independently methyl, ethyl, propyl, butyl, pentyl, or hexyl; among them, propyl is a C3 alkyl (including isomers, such as n-propyl or isopropyl); butyl is a C4 alkyl (including isomers, such as n-butyl, sec-butyl, isobutyl, or tert-butyl); pentyl is a C5 alkyl (including isomers, such as n-pentyl, 1-methyl-butyl, 1-ethyl-propyl, 2-methyl-1-butyl, 3-methyl-1-butyl, isopentyl, tert-pentyl, or neopentyl); hexyl is a C6 alkyl (including isomers, such as n-hexyl or isohexyl).

[0039] The term "alkoxy" used in this application refers to the alkyl as defined above connected via an oxygen bond (-O-).

[0040] In this application, as a group or part of other groups, the term "Cn-Cm aryl" refers to a monocyclic or polycyclic aromatic group (the ring atoms are only carbon atoms) with n to m ring carbon atoms, which has at least one carbon ring with a conjugated π-electron system. Examples of the above aryl units include phenyl, naphthyl, indenyl, azulenyl, fluorenyl, phenanthryl, or anthracenyl. In one embodiment, the aryl is preferably C6-C14 aryl, such as phenyl and naphthyl, and more preferably phenyl.

[0041] In the present application, as a group or as part of other groups, the term "n-m membered heteroaryl" refers to an aromatic group in which the ring atoms contain one or more (e.g., 1, 2, 3, and 4) heteroatoms selected from nitrogen, oxygen, and sulfur, and the number of ring atoms is from n to m. The heteroaryl is a monocyclic, bicyclic, tricyclic, or tetracyclic system, wherein at least one ring is an aromatic ring. Heteroaryls within this definition include, but are not limited to: acridinyl, carbazolyl, cinnolinyl, quinoxalinyl, pyrazolyl, indolyl, benzotriazolyl, furyl, thienyl, benzothienyl, benzofuryl, quinolinyl, isoquinolinyl, oxazolyl, isoxazolyl, pyrazinyl, pyridazinyl, pyridyl, pyrimidinyl, pyrrolyl, tetrahydroquinoline, imidazolyl, triazolyl, tetrazolyl, thiazolyl, isothiazolyl, furazanyl, thiadiazolyl, oxadiazolyl, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, purinyl, pteridinyl, naphthyridinyl, quinazolinyl, phthalazinyl, imidazopyridyl, imidazothiazolyl, imidazoxazolyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, isoindolyl, indazolyl, pyrrolopyridyl, thiophenopyridyl, furanopyridyl, benzothiadiazolyl, benzoxadiazolyl, pyrrolopyrimidinyl, thiophenofuryl. In one embodiment, as preferred examples of "5-18 membered heteroaryl", furyl, thienyl, pyrrolyl, imidazolyl, thiazolyl, pyrazolyl, oxazolyl, isoxazolyl, isothiazolyl, pyridyl, pyrimidinyl, and carbazolyl can be cited, and more preferably carbazolyl.

[0042] As used herein, the term Cn-Cm cycloalkyl refers to a monocyclic or polycyclic alkyl group having n to m carbon atoms, such as C3-C10 cycloalkyl and C3-C6 cycloalkyl. Examples include adamantyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and bicycloheptyl. In one embodiment, C3-C10 cycloalkyl is preferably adamantyl or cyclohexyl.

[0043] In the present application, the defined carbon number range of a group means that it includes any integer number of carbon atoms within the defined range. For example, C1-C20 means that the number of carbon atoms of the group can be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20; C3-C10 means that the number of carbon atoms of the group can be 3, 4, 5, 6, 7, 8, 9, or 10, and so on for the defined carbon number ranges of other groups.

[0044] In the present application, halogen means F, Cl, Br, or I.

[0045] In the present application, the wavy line asterisk both represent the attachment sites of the group.

[0046] Some examples of the present application provide a spirofluorene-based organic compound having the structural characteristics shown in the following formula I:

[0047]

[0048] Wherein, Q is a boron-nitrogen doped polycyclic aryl group, n is 1 or 2, represents a single bond or a non-bonding.

[0049] It can be understood that the Q group can be connected to any position of the spirofluorene group, such as on any benzene ring, not limited to the benzene ring marked in formula I. When n is 2, the two Q groups can be the same or different.

[0050] In some of these examples, the spirofluorene-based organic compound has the structural characteristics shown in the following formula I-1:

[0051]

[0052] R1, R2, R3, R4, R5 and R6 are independently H, deuterium, halogen, C1-C20 alkyl, C1-C20 alkyl substituted by one or more R a substituted C1-C20 alkyl, C1-C20 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, C6-C18 aryl substituted by one or more R a substituted 5-18 membered heteroaryl, 5-18 membered heteroaryl substituted by one or more R a substituted, diphenylamino or diphenylamino substituted by one or more R a substituted diphenylamino.

[0053] R a each occurrence is independently deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkyl substituted by one or more R b substituted C1-C12 alkyl, C1-C12 alkoxy, C3-C12 cycloalkyl, C6-C14 aryl, C6-C14 aryl substituted by one or more R b substituted 5-18 membered heteroaryl, 5-18 membered heteroaryl substituted by one or more R b substituted, diphenylamino or diphenylamino substituted by one or more R b substituted diphenylamino.

[0054] Optionally, R a each occurrence is independently deuterium, fluorine, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, phenyl substituted by at least one C1-C12 alkyl, phenyl substituted by at least one C1-C12 alkoxy, phenyl-C1-C12 alkyl, diphenylamino, diphenylamino substituted by at least one C1-C12 alkyl, carbazolyl or carbazolyl substituted by at least one C1-C12 alkyl.

[0055] R b Each occurrence is independently deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, C6-C14 aryl substituted with one or more R c substituted C6-C14 aryl, 5-18 membered heteroaryl, 5-18 membered heteroaryl substituted with one or more R c substituted 5-18 membered heteroaryl, diphenylamino or diphenylamino substituted with one or more R c substituted diphenylamino.

[0056] Optionally, R b Each occurrence is independently deuterium, fluorine, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, phenyl, phenyl substituted with at least one C1-C12 alkyl, phenyl substituted with at least one C1-C12 alkoxy, phenyl-C1-C12 alkyl, diphenylamino, diphenylamino substituted with at least one C1-C12 alkyl, carbazolyl or carbazolyl substituted with at least one C1-C12 alkyl.

[0057] R c Each occurrence is independently deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, C6-C14 aryl substituted with one or more R d substituted C6-C14 aryl, 5-18 membered heteroaryl, 5-18 membered heteroaryl substituted with one or more R d substituted 5-18 membered heteroaryl, diphenylamino or diphenylamino substituted with one or more R d substituted diphenylamino.

[0058] Optionally, R c Each occurrence is independently deuterium, fluorine, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, phenyl, phenyl substituted with at least one C1-C12 alkyl, phenyl substituted with at least one C1-C12 alkoxy, phenyl-C1-C12 alkyl, diphenylamino, diphenylamino substituted with at least one C1-C12 alkyl, carbazolyl or carbazolyl substituted with at least one C1-C12 alkyl.

[0059] R d Each occurrence is independently deuterium, fluorine, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl or C6-C14 aryl substituted with one or more R e substituted C6-C14 aryl.

[0060] Optionally, R dEach occurrence is independently deuterium, fluorine, a C1-C12 alkyl group, a C1-C12 alkoxy group, a C3-C10 cycloalkyl group, a phenyl group, a phenyl group substituted with at least one C1-C12 alkyl group, a phenyl group substituted with at least one C1-C12 alkoxy group, a carbazolyl group, or a carbazolyl group substituted with at least one C1-C12 alkyl group.

[0061] R e Each occurrence is independently deuterium, fluorine, a C1-C12 alkyl group, a C1-C12 alkoxy group, a C3-C10 cycloalkyl group, or a C6-C14 aryl group.

[0062] Optionally, at least one of R1, R2, R3, R4, R5, and R6 forms a 6- to 8-membered ring or is acyclic with the group it substitutes.

[0063] In some examples, R1, R2, R3, R4, R5, and R6 are independently H, deuterium, fluorine, a C1-C12 alkyl group, a C1-C12 alkoxy group, a C3-C10 cycloalkyl group, a phenyl group, an aryl group substituted with at least one C1-C12 alkyl group, an aryl group substituted with at least one C1-C12 alkoxy group, a phenyl-C1-C12 alkyl group, a diphenylamino group, a diphenylamino group substituted with at least one C1-C12 alkyl group, a diphenylamino group substituted with at least one phenyl-C1-C12 alkyl group, a carbazolyl group, a carbazolyl group substituted with at least one C1-C12 alkyl group, or a carbazolyl group substituted with at least one phenyl-C1-C12 alkyl group.

[0064] Optionally, at least one of R1, R2, R3, R4, R5, and R6 forms a 6- to 8-membered ring or is acyclic with the group it substitutes.

[0065] Optionally, R1, R2, R3, R4, R5, and R6 are independently H, deuterium, fluorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, hexyl, octyl, decyl, methoxy, ethoxy, butoxy, hexyloxy, cyclohexyl, adamantyl, phenyl, 2-methyl-phenyl, 4-methyl-phenyl, 4-ethyl-phenyl, 4-propyl-phenyl, 4-isopropylphenyl, 4-n-butylphenyl,

[0066]

[0067] Optionally, R1, R2, R3, R4, R5, and R6 are independently H, methyl, phenyl, 2-methyl-phenyl,

[0068]

[0069] wherein R g is independently H, methyl, isopropyl, tert-butyl or Optionally, R1, R2, R3, R4, R5 and R6 are independently selected from H, methyl, phenyl, 2-methyl-phenyl,

[0070]

[0071] In some examples, the spirofluorene organic compound has a structural feature shown in Formula I-1a to I-1n as follows:

[0072]

[0073]

[0074] In some examples, the spirofluorene organic compound is one or more of the compounds of Formula BN-1 to BN-258 as follows:

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092] Some other examples of the present application also provide an organic light-emitting composition, including a light-emitting material and a host material, wherein the light-emitting material includes one or more of the spirofluorene organic compounds described above;

[0093] The host material includes a first host material and a second host material, wherein the first host material is a compound containing a carbazole group, and the second host material is one or more of a dicyanobenzene compound and a phosphorescent compound containing metal Ir.

[0094] The above-mentioned organic light-emitting composition has good film-forming properties and narrow spectrum emission characteristics by introducing spirofluorene groups on the basis of boron and nitrogen-doped polycyclic aromatic groups, and adopting the first main material and the second main material at the same time. It is suitable for preparing the functional layer of the device by solution method. The device prepared in this way realizes narrow spectrum TADF emission and has high efficiency and device stability. In some examples, the electroluminescent external quantum efficiency of the device can be as high as 25% or more, and the device life is more than 800 hours.

[0095] In some examples, the first host material includes one or more of the structural compounds shown in Formula H-1 to Formula H-4:

[0096]

[0097] W 1 , W 2 , W 3 , W 4 , W 5 , W 6 , W 7 , W 8 and W 9 independently S or O;

[0098] R 3H , R 4H , R 5H , R 6H , R 7H , R 8H , R 9H , R 10H , R 11H , R 12H , R 13H and R 14H are independently H, deuterium, C1-C6 alkyl or C6-C24 aryl.

[0099] Optionally, R 3H , R 4H , R 5H , R6H , R 7H , R 8H , R 9H , R 10H , R 11H , R 12H , R 13H and R 14H are independently H, deuterium or phenyl.

[0100] In some of these examples, the first host material comprises one or more of the compounds having the structures shown in Formulas H1-1 to H1-44:

[0101]

[0102]

[0103]

[0104]

[0105] In some of these examples, the dicyanobenzene compounds comprise one or more of the compounds having the structures shown in Formulas Ph-2CN-1 to Ph-2CN-6:

[0106]

[0107] Y1, Y2, Y3, Y4, Y5, Y6, Y7, Y8 and Y9 are independently O or S;

[0108] R s1 , R s2 , R s3 , R s 4 , R s5 and R s6 are independently C6-C24 aryl or C12-C36 heteroaryl;

[0109] R s7 to R s39 are independently H, deuterium, C1-C6 alkyl, C1-C6 alkoxy or C6-C24 aryl;

[0110] The alkyl, alkoxy, cycloalkyl, aryl, heteroaryl are unsubstituted or optionally substituted with one or more substituents selected from: deuterium, halogen, -CN, C1-C12 alkyl, C1-C12 alkoxy, C1-C12 haloalkyl, C2-C6 alkenyl, C3-C10 cycloalkyl, C6-C14 aryl and 5-18 membered heteroaryl.

[0111] Optionally, R s1 , R s2 , Rs3 , R s 4 , R s5 and R s6 are independently selected from any one of the following groups:

[0112]

[0113]

[0114] Optionally, R s7 ~R s39 are independently selected from any one of the following groups:

[0115]

[0116] In some examples, the dicyanobenzene compound includes one or more of the compounds having the structures shown in Formulae 2CN-1 to 2CN-60 as follows:

[0117]

[0118]

[0119]

[0120] In some examples, the metal-Ir-containing phosphorescent compound includes one or more of the compounds having the structures shown in Formulae Ir-I to Ir-II as follows:

[0121]

[0122] R r1 ~R r22 are independently hydrogen, deuterium, a C1-C18 alkyl group, a deuterated C1-C18 alkyl group, a C6-C18 aryl group, a C6-C18 aryl group substituted with at least one C1-C18 alkyl group, wherein the dashed line represents that any two of the four included bonds are double bonds spaced apart to form a conjugated structure.

[0123] Optionally, R r1 ~R r22 form a 6- to 20-membered fused ring with the substituted ring or do not form a fused ring, and the fused ring is substituted or unsubstituted with at least one C1-C18 alkyl group.

[0124] In some examples, the metal-Ir-containing phosphorescent compound includes one or more of the compounds having the structures shown in Formulae Ir-1 to Ir-16 as follows:

[0125]

[0126]

[0127] In some other examples of the present application, an organic light-emitting ink material is also provided, which includes one or more of the spirofluorene-based organic compounds and the organic light-emitting compositions as described above, as well as a solvent system.

[0128] In some of these examples, the solvent system includes a first solvent, a surface tension regulator, and a viscosity regulator.

[0129] Optionally, the viscosity of the solvent system is 1 cps to 20 cps, and the surface tension is 20 to 60 dyne / cm. Specifically, the viscosity of the solvent system includes but is not limited to: 1 cps, 1.5 cps, 2 cps, 2.5 cps, 3 cps, 3.5 cps, 4 cps, 4.5 cps, 5 cps, 5.5 cps, 6 cps, 6.5 cps, 7 cps, 8 cps, 9 cps, 10 cps, 12 cps, 15 cps, 17 cps, 20 cps. The surface tension of the solvent system includes but is not limited to: 20 dyne / cm, 25 dyne / cm, 30 dyne / cm, 35 dyne / cm, 40 dyne / cm, 45 dyne / cm, 50 dyne / cm, 55 dyne / cm, 60 dyne / cm.

[0130] Optionally, the solvent system further includes a second solvent.

[0131] In some of these examples, the first solvent is one or more of liquid organic compounds containing a benzene ring structure or liquid naphthalene compounds.

[0132] Optionally, the weight percentage range of the first solvent in the solvent system is 60% to 98%. Specifically, the weight percentage of the first solvent includes but is not limited to: 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, 98%.

[0133] Optionally, the first solvent is a benzoate solvent. Further optionally, the first solvent is one or more of methyl benzoate, ethyl benzoate, ethyl p-methylbenzoate, isobutyl benzoate, 2-ethylhexyl benzoate, and ethyl p-methylbenzoate.

[0134] In some of these examples, the second solvent is one or more of alcohols, ketones, ethers, esters, amides, and aromatic compounds.

[0135] Optionally, the weight percentage range of the second solvent in the solvent system is 0.1% to 30%. Specifically, the weight percentage of the second solvent includes, but is not limited to: 0.1%, 1%, 5%, 10%, 13%, 15%, 16.5%, 18%, 20%, 25%, 30%.

[0136] Optionally, the second solvent is an aromatic hydrocarbon solvent; further optionally, the second solvent is one or more of chlorobenzene, xylene, cyclohexylbenzene, 1-hexylbenzene, 1-hexylnaphthalene, 1-heptylbenzene, 1-octylbenzene, 1-decylbenzene, 4,4'-diethylbiphenyl, 3,4'-diisopropylbiphenyl, and 4,4'-diisopropylbiphenyl.

[0137] In some examples, the surface tension regulator is one or more of a co-solvent, a surfactant, and a small molecule compound that regulates surface tension; the small molecule compound that regulates surface tension includes one or more of imidazole and its derivatives, phenol, and hydroquinone.

[0138] Optionally, the weight percentage range of the surface tension regulator in the solvent system is 0.1% to 5%. Specifically, the weight percentage of the surface tension regulator includes, but is not limited to: 0.1%, 1%, 1.5%, 2%, 2.5%, 3%, 3.5%, 4%, 4.5%, 5%.

[0139] Optionally, the surface tension regulator is one or more of cymene and hydroquinone.

[0140] In some examples, the viscosity regulator is one or more of alcohols, ethers, esters, phenols, and amine compounds;

[0141] Optionally, the weight percentage range of the viscosity regulator in the solvent system is 0.1% - 5%. Specifically, the weight percentage of the viscosity regulator includes, but is not limited to: 0.1%, 1%, 1.5%, 2%, 2.5%, 3%, 3.5%, 4%, 4.5%, 5%.

[0142] Optionally, the viscosity regulator is one or more of benzyl benzoate and butyl stearate.

[0143] In some examples, by weight percentage, the host material is 99.7% to 70.0%, the luminescent material is 0.3% to 30.0%, and the total concentration of the host material and the luminescent material in the organic light-emitting ink material is 5 to 50 mg / mL.

[0144] Specifically, the weight percentage content of the host material includes but is not limited to: 99.7%, 99.2%, 99%, 95%, 90%, 85%, 80%, 75%, 70%.

[0145] Specifically, the weight percentage content of the luminescent material includes but is not limited to: 0.3%, 0.8%, 1%, 3wt%, 5%, 8%, 10%, 15%, 18%, 20%, 23%, 25%, 28%, 30%.

[0146] Specifically, the total concentration of the host material and the luminescent material in the organic light-emitting ink material includes but is not limited to: 5mg / mL, 10mg / mL, 15mg / mL, 20mg / mL, 25mg / mL, 30mg / mL, 35mg / mL, 40mg / mL, 45mg / mL, 50mg / mL. Optionally, the total concentration of the host material and the luminescent material in the organic light-emitting ink material is 10 - 40mg / mL, and further optionally 20 - 40mg / mL.

[0147] Optionally, in the host material, the weight ratio of the first host material to the second host material is 1:20 to 20:1. Specifically, the weight ratio of the first host material to the second host material includes but is not limited to: 1:20, 1:19, 1:18, 1:16, 1:15, 1:13, 1:10, 1:8, 1:6, 1:4, 1:2, 1:1, 2:1, 5:1, 8:1, 10:1, 13:1, 15:1, 18:1, 20:1.

[0148] Without limitation, the organic light-emitting ink material is used for preparing a light-emitting layer.

[0149] The preparation method of the organic light-emitting ink material as described above can be prepared by traditional methods in the art.

[0150] In some examples, the preparation method of the organic light-emitting ink material includes the following steps:

[0151] Mix and dissolve the luminescent material, host material and solvent system, and filter to prepare the organic light-emitting ink material.

[0152] Optionally, the method of mixing and dissolving is stirring under the condition of 20°C - 80°C.

[0153] In some examples, the preparation method of the organic light-emitting ink material includes the following steps:

[0154] (1) Dissolve the main material and the luminescent material in a first solvent, and stir for 0.5 - 24 hours under the condition of 20°C - 80°C. Determine whether a second solvent needs to be added. If so, add the second solvent to the above system and continue to stir for 0.5 - 24 hours; if not, proceed to the next step of the experiment.

[0155] (2) Take a surface tension regulator and a viscosity regulator and add them to the above mixture, and stir for 0.5 - 24 hours under the condition of 20°C - 80°C until the mixture is transparent and clear.

[0156] (3) Filter the above clear mixture using a microporous membrane with a pore size of 0.22 μm or less.

[0157] In some other examples of the present application, there is also provided an application of the spirofluorene-based organic compound, the organic light-emitting composition or the organic light-emitting ink material as described above in the preparation of organic electronic devices.

[0158] In some other examples of the present application, there is also provided an organic electronic device, including a functional layer, where the functional layer contains one or more of the spirofluorene-based organic compounds and the organic light-emitting compositions as described above, or the functional layer is prepared from the organic light-emitting ink material as described above.

[0159] Optionally, the preparation method is a solution method. Further optionally, the solution method includes inkjet printing, relief printing, screen printing, dip coating, spin coating, blade coating, roller printing, reverse roller printing, plate printing, rotary printing, spraying, brush coating, pad printing or slot die coating.

[0160] In some of these examples, the organic electronic device is an organic light-emitting diode, an organic solar cell, an organic field-effect transistor, an organic light-emitting field-effect transistor, an organic laser, an organic spintronic device, an organic sensor or an organic plasmonic emission diode.

[0161] In some of these examples, the organic electronic device includes a substrate and an anode layer, the functional layer and a cathode layer formed on the substrate in sequence. The functional layer includes a light-emitting layer, and the light-emitting layer contains one or more of the spirofluorene-based organic compounds and the organic light-emitting compositions as described above, or the light-emitting layer is prepared from the organic light-emitting ink material as described above. Further optionally, the functional layer further includes one or more of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer.

[0162] Some other examples of the present application also provide a display device or a lighting device, including the organic electronic device as described above.

[0163] For the experimental parameters not specified in the following specific examples, priority shall be given to the guidance provided in this application document. It is also possible to refer to experimental manuals in the art or other experimental methods known in the art, or to the experimental conditions recommended by the manufacturer.

[0164] The raw materials and reagents involved in the following specific examples can be obtained commercially, or can be prepared by those skilled in the art according to known means.

[0165] Synthesis reaction route of the general formula I compound:

[0166] (1) When n = 1, the general formula of the reaction route is:

[0167]

[0168] (2) When n = 2 and the Q groups are the same, the general formula of the reaction route is:

[0169]

[0170] (3) When n = 2 and the two Q groups are different, the general formula of the reaction route is:

[0171]

[0172] The raw materials used in the compound synthesis are: First raw material:

[0173]

[0174] Second raw material:

[0175]

[0176] Third raw material (ligand)

[0177]

[0178] Synthesis experiment of the representative compound BN-2:

[0179]

[0180] Synthesis and Characterization of Compound BN-2-A: The first raw material 1-B (22.1 g, 50.0 mmol), the second raw material 2-A (14.7 g, 60.0 mmol), and potassium carbonate (10.4 g, 75.0 mmol) were dissolved in a mixed solvent of 120 mL of tetrahydrofuran (THF) and 40 mL of water. Under nitrogen, tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol) was added, and the temperature was raised to 60 °C and stirred continuously for 6 hours. After the reaction was completed and cooled to room temperature, it was washed three times with 200 mL of dichloromethane and 200 mL of water respectively. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether) to obtain 22.8 g of a white solid (yield 94.8%). It was confirmed to be the target product by mass spectrometry, MS: 480.12 (calculated value: 480.09).

[0181] Synthesis and Characterization of Compound BN-2-B: Compound BN-2-A (21.6 g, 45.0 mmol), the third raw material 3-A (41.5 g, 148.5 mmol), and cesium carbonate (58.1 g, 178.2 mmol) were dissolved in 600 mL of N,N-dimethylformamide (DMF). Under nitrogen, it was heated to 130 °C and stirred continuously for 12 hours. After the reaction was completed and cooled to room temperature, the reaction system was poured into 2 L of ice water and stirred continuously. The precipitated precipitate was filtered under reduced pressure, and the filter cake was recrystallized with dichloromethane / methanol to obtain 50.1 g of a white solid (yield 88.5%). It was confirmed to be the target product by mass spectrometry, MS: 1257.88 (calculated value: 1257.67).

[0182] Synthesis and Characterization of Compound BN-2: Compound BN-2-B (37.7 g, 30.0 mmol) was dissolved in 100 mL of tert-butylbenzene. At 0 °C, under nitrogen, tert-butyllithium (27.7 mL, 36.0 mmol, 1.3 M) was added dropwise. After the temperature was raised to 60 °C and lithiated for 2 hours, it was cooled to 0 °C, and BBr3 (11.2 g, 45.0 mmol) was added dropwise. After raising the temperature to room temperature and stirring for 1 hour, it was cooled to 0 °C, and N,N-diisopropylethylamine (DIEA) (5.8 g, 45.0 mmol) was added dropwise. The temperature was raised to 120 °C and stirred continuously for 8 hours. After the reaction was completed and cooled to room temperature, the reaction was quenched with 10 mL each of methanol and water. The reaction system was washed three times each with 200 mL of dichloromethane and water. The organic phase was concentrated and purified by column chromatography (eluent: dichloromethane / petroleum ether = 1:9) to obtain 11.9 g of an orange-yellow solid (yield 32.1%). It was confirmed to be the target product by mass spectrometry and elemental analysis, MS: 1231.67 (calculated value: 1231.69); elemental analysis: C, 88.67; H, 7.02; N, 3.43 (calculated value: C, 88.68; H, 7.03; N, 3.41).

[0183] Synthesis experiment of representative compound BN-19:

[0184]

[0185] Synthesis and characterization of compound BN-19-A: The synthesis of compound BN-19-A was similar to that of compound BN-2-A. The first raw material 1-C (22.1 g, 50.0 mmol) was used instead of the first raw material 1-B, and the dosages of other reactants, reaction conditions and treatment methods were the same. After column chromatography, 20.9 g of white solid was obtained (yield: 86.9%). It was confirmed as the target product by mass spectrometry, MS: 480.10 (calculated value: 480.09).

[0186] Synthesis and characterization of compound BN-19-B: The synthesis of compound BN-19-B was similar to that of compound BN-2-B. Compound BN-19-A (21.6 g, 45.0 mmol) was used instead of compound BN-2-A, and the third raw material 3-C (47.4 g, 148.5 mmol) was used instead of the third raw material 3-A. The dosages of other reactants, reaction conditions and treatment methods were the same. After recrystallization, 56.0 g of white solid was obtained (yield 90.3%). It was confirmed as the target product by mass spectrometry, MS: 1378.50 (calculated value: 1378.48).

[0187] Synthesis and characterization of compound BN-19: The synthesis of compound BN-19 was similar to that of compound BN-2. Compound BN-19-B (41.4 g, 30.0 mmol) was used instead of compound BN-2-B, and the dosages of other reactants, reaction conditions and treatment methods were the same. After column chromatography, 10.4 g of orange solid was obtained (yield: 25.6%). It was confirmed as the target product by mass spectrometry and elemental analysis, MS: 1352.50 (calculated value: 1352.51); elemental analysis: C, 91.51; H, 4.63; N, 3.11 (calculated value: C, 91.47; H, 4.62; N, 3.11).

[0188] Synthesis experiment of representative compound BN-69:

[0189]

[0190] Synthesis and Characterization of Compound BN-69-A: The synthesis of compound BN-69-A was similar to that of compound BN-2-A. The first raw material 1-A (22.1 g, 50.0 mmol) was used instead of the first raw material 1-B, and the second raw material 2-B (14.7 g, 60.0 mmol) was used instead of the second raw material 2-A. The dosages of other reactants, reaction conditions, and treatment methods were the same. After column chromatography, 21.7 g of white solid was obtained (yield: 90.3%). It was confirmed as the target product by mass spectrometry, MS: 480.11 (calculated value: 480.09).

[0191] Synthesis and Characterization of Compound BN-69-B: Compound BN-69-A (57.7 g, 120.0 mmol), the third raw material 3-G (21.2 g, 60.0 mmol), and cesium carbonate (29.3 g, 90.0 mmol) were dissolved in 200.0 mL of DMF. Under nitrogen atmosphere, the temperature was raised to 120 °C and kept warm for 8 hours. After the reaction ended and cooled to room temperature, it was washed three times with 500 mL of dichloromethane and water respectively. The organic layer was concentrated and purified by column chromatography (eluent: dichloromethane / petroleum ether = 1:6) to obtain 31.7 g of white solid (yield: 52.8%). It was confirmed as the target product by mass spectrometry, MS: 813.26 (calculated value: 813.30).

[0192] Synthesis and Characterization of Compound BN-69-C: Compound BN-69-B (36.6 g, 45.0 mmol), the third raw material 3-A (27.7 g, 99.0 mmol), and cesium carbonate (48.4 g, 148.5 mmol) were dissolved in 200.0 mL of DMF. Under nitrogen atmosphere, the temperature was raised to 120 °C and kept warm for 10 hours. After the reaction ended and cooled to room temperature, the reaction system was poured into 800 mL of ice water and stirred continuously. The precipitated solid was filtered under reduced pressure. The filter cake was recrystallized with dichloromethane / methanol to obtain 56.2 g of white solid (yield 93.7%). It was confirmed as the target product by mass spectrometry, MS: 1332.71 (calculated value: 1332.69).

[0193] Synthesis and Characterization of Compound BN-69: The synthesis of compound BN-69 was similar to that of compound BN-2. Compound BN-69-B (40.0 g, 30.0 mmol) was used instead of compound BN-2-B. The dosages of other reactants, reaction conditions, and treatment methods were the same. After column chromatography, 11.9 g of orange solid was obtained (yield: 30.5%). It was confirmed as the target product by mass spectrometry and elemental analysis, MS: 1305.70 (calculated value: 1305.71); elemental analysis: C, 89.18; H, 6.80; N, 3.23 (calculated value: C, 89.17; H, 6.79; N, 3.22).

[0194] Synthesis experiment of representative compound BN-88:

[0195]

[0196] Synthesis and characterization of compound BN-88-A: The synthesis of compound BN-88-A was similar to that of compound BN-69-A. The first raw material 1-D (22.1 g, 50.0 mmol) was used instead of the first raw material 1-A, and the dosages of other reactants, reaction conditions and treatment methods were the same. After column chromatography, 22.5 g of white solid was obtained (yield: 93.6%). It was confirmed as the target product by mass spectrometry, MS: 480.07 (calculated value: 480.09).

[0197] Synthesis and characterization of compound BN-88-B: The synthesis of compound BN-88-B was similar to that of compound BN-69-B. Compound BN-88-A (57.7 g, 120.0 mmol) was used instead of compound BN-69-A, and the third raw material 3-I (26.5 g, 60.0 mmol) was used instead of the third raw material 3-G. The dosages of other reactants, reaction conditions and treatment methods were the same. After column chromatography, 33.7 g of white solid was obtained (yield: 62.3%). It was confirmed as the target product by mass spectrometry, MS: 902.35 (calculated value: 902.32).

[0198] Synthesis and characterization of compound BN-88-C: The synthesis of compound BN-88-C was similar to that of compound BN-69-C. Compound BN-88-B (40.6 g, 45.0 mmol) was used instead of compound BN-69-B, and the dosages of other reactants, reaction conditions and treatment methods were the same. After recrystallization, 58.7 g of white solid was obtained (yield: 91.7%). It was confirmed as the target product by mass spectrometry, MS: 1421.73 (calculated value: 1421.71).

[0199] Synthesis and characterization of compound BN-88: The synthesis of compound BN-88 was similar to that of compound BN-2. Compound BN-69-B (42.6 g, 30.0 mmol) was used instead of compound BN-2-B, and the dosages of other reactants, reaction conditions and treatment methods were the same. After column chromatography, 12.3 g of orange solid was obtained (yield: 29.3%). It was confirmed as the target product by mass spectrometry and elemental analysis, MS: 1395.78 (calculated value: 1395.74); elemental analysis: C, 88.64; H, 6.56; N, 4.02 (calculated value: C, 88.64; H, 6.57; N, 4.01).

[0200] Synthesis experiment of representative compound BN-169:

[0201]

[0202] Synthesis and Characterization of Compound BN-169-A: The first raw material 1-E (28.4 g, 50.0 mmol), the second raw material 2-A (27.0 g, 110.0 mmol) and potassium carbonate (27.6 g, 200.0 mmol) were dissolved in a mixed solution of 100 mL of water and 400 mL of THF. Tetrakis(triphenylphosphine)palladium (1.73 g, 1.5 mmol) was added under nitrogen atmosphere, and the temperature was raised to 70 °C and stirred continuously for 12 hours. After the reaction was completed and cooled to room temperature, it was washed three times with 500 mL of dichloromethane and water respectively. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether) to obtain 23.1 g of white solid (yield: 71.6%). It was confirmed as the target product by mass spectrometry, MS: 644.03 (calculated value: 644.05).

[0203] Synthesis and Characterization of Compound BN-169-B: Compound BN-169-A (21.6 g, 15.0 mmol), the third raw material 3-A (30.1 g, 108.0 mmol) and cesium carbonate (42.4 g, 130.0 mmol) were dissolved in 400 mL of DMF. It was heated to 130 °C under nitrogen atmosphere and stirred continuously for 12 hours. After the reaction was completed and cooled to room temperature, the reaction system was poured into 1 L of ice water and stirred continuously. The precipitated precipitate was filtered under reduced pressure. The filter cake was recrystallized with dichloromethane / methanol to obtain 24.0 g of white solid (yield 72.6%). It was confirmed as the target product by mass spectrometry, MS: 2201.24 (calculated value: 2201.21).

[0204] Synthesis and Characterization of Compound BN-169: Dissolve compound BN-169-B (22.0 g, 10.0 mmol) in 120 mL of tert-butylbenzene. At 0 °C and under nitrogen, add tert-butyllithium (23.1 mL, 30.0 mmol, 1.3 M) dropwise. After heating to 60 °C and lithiating for 6 hours, cool to 0 °C, add BBr3 (11.2 g, 45.0 mmol) dropwise, raise the temperature to room temperature and stir for 4 hours, then cool to 0 °C, add N,N-diisopropylethylamine (DIEA) (5.8 g, 45.0 mmol) dropwise, and heat to 120 °C and continue stirring for 24 hours. After the reaction is completed and cooled to room temperature, quench the reaction with 10 mL each of methanol and water. Wash the reaction system three times each with 200 mL of dichloromethane and water. After concentrating the organic phase, purify it by column chromatography (eluent: dichloromethane / petroleum ether = 1:6) to obtain 4.4 g of an orange solid (yield 20.5%). It is confirmed as the target product by mass spectrometry and elemental analysis. MS: 2147.22 (calculated value: 2147.29); Elemental analysis: C, 87.75; H, 7.30; N, 3.94 (calculated value: C, 87.76; H, 7.32; N, 3.91).

[0205] Synthesis Experiment of Representative Compound BN-180:

[0206]

[0207] Synthesis and Characterization of Compound BN-180-A: The synthesis of compound BN-180-A is similar to that of compound BN-169-A. Use the first raw material 1-F (28.4 g, 50.0 mmol) instead of the first raw material 1-E, use the second raw material 2-B (27.0 g, 110.0 mmol) instead of the second raw material 2-A, and keep other reaction conditions and treatment methods the same. After column chromatography, 25.7 g of a white solid is obtained (yield: 79.6%). It is confirmed as the target product by mass spectrometry. MS: 644.08 (calculated value: 644.05).

[0208] Synthesis and Characterization of Compound BN-180-B: The synthesis of compound BN-180-B is similar to that of compound BN-169. Use compound BN-180-A (21.6 g, 15.0 mmol) instead of compound BN-169-A, use the third raw material 3-G (38.1 g, 108.0 mmol) instead of the third raw material 3-A, and keep other reaction conditions and treatment methods the same. After recrystallization, 26.2 g of a white solid is obtained (yield 66.1%). It is confirmed as the target product by mass spectrometry. MS: 2645.34 (calculated value: 2645.31).

[0209] Synthesis and Characterization of Compound BN-180: The synthesis of compound BN-180 was similar to that of compound BN-169. Compound BN-180-B (26.4 g, 10.0 mmol) was used instead of compound BN-169-B, and other reaction conditions and treatment methods were the same. After purification by column chromatography, 5.6 g of orange-red solid was obtained (yield 21.8%). It was confirmed as the target product by mass spectrometry and elemental analysis. MS: 2592.32 (calculated value: 2592.33); Elemental analysis: C, 89.42; H, 6.51; N, 3.24 (calculated value: C, 89.39; H, 6.53; N, 3.24).

[0210] Synthesis Experiment of Representative Compound BN-217:

[0211]

[0212] Synthesis and Characterization of Compound BN-217-A: The first raw material 1-E (28.4 g, 50.0 mmol), the second raw material 2-A (13.5 g, 55.0 mmol) and potassium carbonate (8.3 g, 60.0 mmol) were dissolved in a mixed solution of 30 mL of water and 120 mL of THF. Tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol) was added under nitrogen atmosphere, and the temperature was raised to 70 °C and stirred continuously for 6 hours. After the reaction was completed and cooled to room temperature, it was washed three times with 200 mL of dichloromethane and water respectively. The organic phase was concentrated and purified by column chromatography (developing agent: petroleum ether) to obtain 16.9 g of white solid (yield: 55.7%). It was confirmed as the target product by mass spectrometry analysis. MS: 606.22 (calculated value: 606.17).

[0213] Synthesis and Characterization of Compound BN-217-B: Compound BN-217-A (28.4 g, 25.0 mmol), the second raw material 2-A (7.4 g, 30.0 mmol) and potassium carbonate (5.2 g, 37.5 mmol) were dissolved in a mixed solution of 20 mL of water and 80 mL of THF. Tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol) was added under nitrogen atmosphere, and the temperature was raised to 70 °C and stirred continuously for 6 hours. After the reaction was completed and cooled to room temperature, it was washed three times with 100 mL of dichloromethane and water respectively. The organic phase was concentrated and purified by column chromatography (developing agent: petroleum ether) to obtain 14.0 g of white solid (yield: 86.8%). It was confirmed as the target product by mass spectrometry analysis. MS: 644.08 (calculated value: 644.05).

[0214] Synthesis and Characterization of Compound BN-217-C: Compound BN-217-B (12.9 g, 20.0 mmol), the third raw material 3-A (11.2 g, 40.0 mmol), and cesium carbonate (15.6 g, 48.0 mmol) were dissolved in 150 mL of DMF, and the mixture was kept at 120 °C for 8 hours under nitrogen. After the reaction was completed and cooled to room temperature, it was washed three times with 200 mL of dichloromethane and water respectively. The organic phase was concentrated and purified by column chromatography (eluent: dichloromethane / petroleum ether = 1:3) to obtain 14.8 g of a white solid (yield: 63.8%). It was confirmed to be the target product by mass spectrometry analysis, MS: 1162.42 (calculated value: 1162.44).

[0215] Synthesis and Characterization of Compound BN-217-D: Compound BN-217-C (13.9 g, 12.0 mmol), the third raw material 3-G (21.2 g, 60.0 mmol), and cesium carbonate (29.3 g, 90.0 mmol) were dissolved in 200 mL of DMF, and the mixture was kept at 150 °C for 12 hours under nitrogen. After the reaction was completed and cooled to room temperature, the reaction system was poured into 500 mL of ice water and stirred continuously. The precipitated solid was filtered under reduced pressure, and the filter cake was recrystallized with dichloromethane / methanol to obtain 24.4 g of a white solid (yield 81.6%). It was confirmed to be the target product by mass spectrometry analysis, MS: 2495.24 (calculated value: 2495.27).

[0216] Synthesis and Characterization of Compound BN-217: The synthesis of Compound BN-217 was similar to that of Compound BN-169. Compound BN-217-D (25.0 g, 10.0 mmol) was used instead of Compound BN-169-B, and other reaction conditions and treatment methods were the same. After purification by column chromatography, 4.9 g of an orange-red solid was obtained (yield 19.9%). It was confirmed to be the target product by mass spectrometry and elemental analysis, MS: 2443.29 (calculated value: 2445.33); elemental analysis: C, 88.95; H, 6.74; N, 3.43 (calculated value: C, 88.92; H, 6.76; N, 3.44).

[0217] Compounds not given in the following examples can be prepared by methods similar to the preparation methods described above, and the products were all verified by mass spectrometry and elemental analysis. See Table 1 for details.

[0218] Table 1: Raw materials and characterization of Compounds BN-1 to BN-258.

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228] Examples of ink preparation:

[0229] Some representative organic light-emitting ink formulations are given below. See Tables 2 and 3 for details.

[0230] The solvents specifically used are as follows:

[0231] First solvent: Methyl benzoate (S1-1), Ethyl p-toluate (S1-2), Ethyl benzoate (S1-3), Ethyl hexyl benzoate (S1-4), Isobutyl benzoate (S1-5), Ethyl hexyl p-toluate (S1-6);

[0232] Second solvent: Chlorobenzene (S2-1), Xylene (S2-2), Cyclohexylbenzene (S2-3), 1-Hexylnaphthalene (S2-4), 4,4'-Diethylbiphenyl (S2-5), 4,4'-Diisopropylbiphenyl (S2-6), 1-Octylbenzene (S2-7);

[0233] Surface tension regulator: Cumene (S3-1), Hydroquinone (S3-2);

[0234] Viscosity regulator: Benzyl benzoate (S4-1), Butyl stearate (S4-2).

[0235] Table 2. Solvent Formulation of Organic Light-Emitting Material Ink

[0236]

[0237] Table 3. Organic Light-Emitting Ink Formulation

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244] The preparation method of the above-mentioned organic light-emitting ink is as follows:

[0245] (1) Weigh the host material and the luminescent material according to the ratio;

[0246] (2) Dissolve the weighed host material and luminescent material in the first solvent according to the concentration, stir at 60 °C for 10 hours, add the second solvent to the above system according to the ratio, and continue to stir for 5 hours;

[0247] (3) Weigh the surface tension regulator and the viscosity regulator according to the ratio, add them to the mixed solution in step (2), and stir at 60 °C for 1 hour until the mixed solution is transparent and clear;

[0248] (4) Filter the above-mentioned clear mixed solution with a 0.22-micron microporous filter membrane to obtain the organic light-emitting ink.

[0249] Examples of electroluminescent devices

[0250] Some representative examples of electroluminescent devices are given below. The molecular structures of some materials involved in the device examples and the comparative device examples are as follows. Among them, Pedot:PSS is a product of model AI4083 purchased from Heraeus, PFI is a NafionTM perfluorinated resin solution purchased from sigma-aldrich, and poly-HTL is purchased from Xi'an Baolaitai:

[0251]

[0252]

[0253] Preparation process of organic electroluminescent devices:

[0254] The structure of the device is as Figure 1 shown, where 1 is the ITO anode, 2 is the first hole transport layer, 3 is the second hole transport layer, 4 is the light-emitting layer, 5 is the first electron transport layer, 6 is the second electron transport layer, 7 is the electron injection layer, and 8 is the metal cathode.

[0255] The device preparation process is as follows:

[0256] (1) Substrate treatment: The transparent ITO glass is used as the substrate material for fabricating the device. First, it is ultrasonically treated with 5% ITO cleaning solution for 30 min, and then ultrasonically washed successively with distilled water (twice), acetone (twice), and isopropyl alcohol (twice). Finally, the ITO glass is stored in isopropyl alcohol. Before each use, the surface of the ITO glass is carefully wiped with acetone cotton balls and isopropyl alcohol cotton balls, dried after being rinsed with isopropyl alcohol, and then treated with plasma for 5 min for standby. The fabrication of the device is completed by combining spin coating and vacuum evaporation processes.

[0257] (2) Preparation of hole injection layer and hole transport layer: PEDOT:PSS and PFI are formulated into the first hole transport layer mixture in a mass ratio of 1:5 by spin coating process. 200 μL of the first hole transport layer mixture is dropped onto the ITO glass and spin-coated at a speed of 3500 rpm / min for 40 s, and then annealed and dried at 150 °C for 15 min to form the first hole transport layer with a thickness of 40 nm; The second hole transport material poly-HTL is dissolved using chlorobenzene as a solvent to obtain a second hole transport layer solution with a concentration of 8 mg / ml. 100 μL of the second hole transport layer solution is dropped onto the above first hole transport layer and spin-coated at a speed of 1500 rpm / min for 60 s, and then annealed and dried at 100 °C for 1 h to form the second hole transport layer with a thickness of 20 nm.

[0258] (3) Preparation of light-emitting layer: The organic light-emitting ink is formed on the second hole transport layer by spin coating process, and is treated under a gas pressure condition of 50000 Pa for 10 minutes through vacuum film-forming process, and then treated under a gas pressure condition of 10 Pa for 5 minutes for drying and film-forming, and then baked at 120 °C for 20 minutes to form a light-emitting layer with a thickness of 40 nm.

[0259] (4) Preparation of electron transport layer, electron injection layer and metal electrode: The first electron transport layer, the second electron transport layer, the electron injection layer and the metal electrode are prepared by evaporation process. When the vacuum degree of the vacuum evaporation system reaches below 5×10 -4 Pa, evaporation starts. The deposition rate is measured by the Sains film thickness gauge. The organic electron transport layer, LiF electron injection layer and metal Al electrode are successively deposited on the light-emitting layer by vacuum evaporation process (the specific device structure is shown in the following effect examples). Among them, the deposition rate of the organic material is The deposition rate of LiF is The deposition rate of Al is

[0260] The characteristics of the device such as current, voltage, luminance, and emission spectrum were synchronously measured using a Photo Research PR 655 spectral scanning luminance meter and a Keithley K2400 digital source meter system. The performance tests of the device were carried out at room temperature and ambient atmosphere. The external quantum efficiency (EQE) of the device was calculated by combining the current density, luminance, and electroluminescence spectrum with the visibility function under the condition that the emission was Lambertian distribution.

[0261] Device Examples 1 - n (n = 1 - 135)

[0262] In the organic electroluminescent devices (with the structure as Figure 1 shown) of Device Examples 1 - n (n = 1 - 135), PEDOT:PSS:PFI was used as the first hole transport layer, Poly-HTL was used as the second hole transport layer, Ink-n (n = 1 - 258) was prepared into the light-emitting layer by spin coating, DMFBD-TRZ was used as the first electron transport layer, Na-An-BI was used as the second electron transport layer, Liq was used as the electron injection layer, and Al was used as the metal cathode. The structure of the organic electroluminescent device in the Effect Example was [ITO / PEDOT:PSS:PFI(60 nm) / Poly-HTL(15 nm) / EML(35 nm) / DMFBD-TRZ(10 nm) / Na-An-BI(30 nm) / Liq(2 nm) / Al(100 nm)].

[0263] The performance data of the device examples are shown in Table 4. The device lifetime (T50, hours) in Table 4 refers to the time required for the luminance of the device to decrease to 50% of the initial luminance at a luminance of 300 cd / m 2 brightness.

[0264] Table 4. Electroluminescent Device Examples

[0265]

[0266]

[0267]

[0268]

[0269] The formulation of the ink for the comparative example is shown in Table 5 below, and the preparation method is the same as that of the example.

[0270] Table 5

[0271]

[0272] Device Comparative Examples D - n (n = 1 - 11)

[0273] In the organic electroluminescent device in Device Embodiment D-n (n = 1 - 11) (the structure is as Figure 1 shown), PEDOT:PSS:PFI is used as the first hole transport layer, Poly-HTL is used as the second hole transport layer, Ink-Rn (n = 1 - 11) is prepared by spin coating to form the emitting layer EML, DMFBD-TRZ is used as the first electron transport layer, Na-An-BI is used as the second electron transport layer, Liq is used as the electron injection layer, and Al is used as the metal cathode. The structure of the comparative organic electroluminescent device is [ITO / PEDOT:PSS:PFI(60nm) / Poly-HTL(15nm) / EML(35nm) / DMFBD-TRZ(10nm) / Na-An-BI(30nm) / Liq(2nm) / Al(100nm)].

[0274] The performance data of the device comparative example are shown in Table 6. The device lifetime (T50, hours) in Table 6 refers to the time required for the brightness of the device to decrease to 50% of the initial brightness at a brightness of 300 cd / m 2 brightness.

[0275] Table 6. Comparative Examples of Electroluminescent Devices

[0276]

[0277]

[0278] Based on the data of the above device embodiments (Table 4) and the data of the comparative device embodiments (Table 6), it can be seen that when the organic light-emitting materials and the ink materials configured thereof in the present application are applied to electroluminescent devices, obvious technical advantages are shown. When the luminescent compounds BN-n (n = 1 - 258) and H1-i (i = 1 - 44) in the present application are combined alone or the luminescent materials in the present application and 2CN-j (j = 1 - 60) are combined alone, their electroluminescent performance deteriorates significantly. In addition, compared with the organic light-emitting ink materials prepared from some publicly disclosed luminescent compounds Rm (m = 1 - 8), the organic light-emitting ink materials prepared from the luminescent compounds BN-n (n = 1 - 258) in the present application also show significantly excellent performance.

[0279] The technical features of the above-described embodiments can be combined arbitrarily. For the sake of brevity of description, not all possible combinations of the technical features in the above embodiments are described. However, as long as there is no contradiction in the combination of these technical features, it should be considered to be within the scope described in this specification.

[0280] The above-described embodiments merely represent several implementation manners of the present application, facilitating a specific and detailed understanding of the technical solution of the present application. However, it should not be construed as a limitation on the scope of patent protection of the application. It should be noted that for those of ordinary skill in the art, without departing from the concept of the present application, several modifications and improvements can still be made, and these all fall within the protection scope of the present application. It should be understood that the technical solutions obtained by those skilled in the art through logical analysis, reasoning, or limited experiments based on the technical solution provided by the present application are all within the protection scope of the appended claims of the present application. Therefore, the protection scope of the patent of the present application shall be subject to the content of the appended claims, and the specification can be used to interpret the content of the claims.

Claims

1. A spirofluorene-based organic compound, characterized in that, It has the structural features shown in Formula I below: Among them, Q is a boron-nitrogen doped polycyclic aryl group, n is 1 or 2, indicating a single bond or non-bonding.

2. The spirofluorene-based organic compound according to claim 1, wherein It has the structural features shown in Formula I-1 below: R1, R2, R3, R4, R5 and R6 are independently H, deuterium, halogen, C1-C20 alkyl, C1-C20 alkyl substituted with one or more R a substituted C1-C20 alkyl, C1-C20 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, C6-C18 aryl substituted with one or more R a substituted 5-18 membered heteroaryl, diphenylamino or diphenylamino substituted with one or more R a substituted 5-18 membered heteroaryl; a ​ R a Each occurrence is independently deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkyl substituted with one or more R b substituted C1-C12 alkyl, C1-C12 alkoxy, C3-C12 cycloalkyl, C6-C14 aryl, C6-C14 aryl substituted with one or more R b substituted C6-C14 aryl, 5-18 membered heteroaryl, 5-18 membered heteroaryl substituted with one or more R b substituted 5-18 membered heteroaryl, diphenylamino or diphenylamino substituted with one or more R b substituted diphenylamino; optionally, R a Each occurrence is independently deuterium, fluorine, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, phenyl substituted with at least one C1-C12 alkyl, phenyl substituted with at least one C1-C12 alkoxy, phenyl-C1-C12 alkyl, diphenylamino, diphenylamino substituted with at least one C1-C12 alkyl, carbazolyl or carbazolyl substituted with at least one C1-C12 alkyl; R b Each occurrence is independently deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, C6-C14 aryl substituted with one or more R c substituents, 5-18 membered heteroaryl, 5-18 membered heteroaryl substituted with one or more R c substituents, diphenylamino or diphenylamino substituted with one or more R c substituents; optionally, R b Each occurrence is independently deuterium, fluorine, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, phenyl, phenyl substituted with at least one C1-C12 alkyl, phenyl substituted with at least one C1-C12 alkoxy, phenyl-C1-C12 alkyl, diphenylamino, diphenylamino substituted with at least one C1-C12 alkyl, carbazolyl or carbazolyl substituted with at least one C1-C12 alkyl; R c each occurrence independently is deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, C6-C14 aryl substituted with one or more R d substituents, 5-18 membered heteroaryl, 5-18 membered heteroaryl substituted with one or more R d substituents, diphenylamino or diphenylamino substituted with one or more R d substituents; optionally, R c each occurrence independently is deuterium, fluorine, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, phenyl, phenyl substituted with at least one C1-C12 alkyl, phenyl substituted with at least one C1-C12 alkoxy, phenyl-C1-C12 alkyl, diphenylamino, diphenylamino substituted with at least one C1-C12 alkyl, carbazolyl or carbazolyl substituted with at least one C1-C12 alkyl; R d Each occurrence is independently deuterium, fluorine, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl or C6-C14 aryl substituted by one or more R e Optionally, R d Each occurrence is independently deuterium, fluorine, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, phenyl, phenyl substituted by at least one C1-C12 alkyl, phenyl substituted by at least one C1-C12 alkoxy, carbazolyl or carbazolyl substituted by at least one C1-C12 alkyl; R e Each occurrence is independently deuterium, fluorine, a C1-C12 alkyl group, a C1-C12 alkoxy group, a C3-C10 cycloalkyl group, or a C6-C14 aryl group; Optionally, at least one of R1, R2, R3, R4, R5, and R6 forms a 6- to 8-membered ring or does not form a ring with the group it substitutes.

3. The spirofluorene-based organic compound according to claim 2, characterized in that, R1, R2, R3, R4, R5, and R6 are independently H, deuterium, fluorine, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, phenyl, aryl substituted with at least one C1-C12 alkyl, aryl substituted with at least one C1-C12 alkoxy, phenyl-C1-C12 alkyl, diphenylamino, diphenylamino substituted with at least one C1-C12 alkyl, diphenylamino substituted with at least one phenyl-C1-C12 alkyl, carbazolyl, carbazolyl substituted with at least one C1-C12 alkyl, or carbazolyl substituted with at least one phenyl-C1-C12 alkyl; Optionally, at least one of R1, R2, R3, R4, R5, and R6 forms a 6- to 8-membered ring or does not form a ring with the group it substitutes; Optionally, R1, R2, R3, R4, R5 and R6 are independently selected from H, methyl, phenyl, 2-methyl-phenyl, 4. The spirofluorene-based organic compound according to claim 3, characterized in that, It has the structural features shown in any one of Formulae I-1a to I-1n below:

5. The spirofluorene-based organic compound according to any one of claims 1 to 4, characterized in that, The spirofluorene-based organic compound is one of the compounds of Formulae BN-1 to BN-258 below:

6. An organic light-emitting composition, characterized in that, It includes a light-emitting material and a host material, and the light-emitting material includes one or more of the spirofluorene-based organic compounds described in any one of Claims 1 to 5; The host material includes a first host material and a second host material. The first host material is a compound containing a carbazolyl group, and the second host material is one or more of a dicyanobenzene-based compound and a phosphorescent compound containing metal Ir.

7. The organic light-emitting composition according to claim 6, characterized in that, The first host material includes one or more of the compounds having the structural formulae shown in Formulae H-1 to H-4 below: W 1 、W 2 、W 3 、W 4 、W 5 、W 6 、W 7 、W 8 and W 9 are independently S or O; R 3H 、R 4H 、R 5H 、R 6H 、R 7H 、R 8H 、R 9H 、R 10H 、R 11H 、R 12H 、R 13H and R 14H are independently H, deuterium, C1-C6 alkyl or C6-C24 aryl; Optionally, R 3H , R 4H , R 5H , R 6H , R 7H , R 8H , R 9H , R 10H , R 11H , R 12H , R 13H , and R 14H are independently H, deuterium, or phenyl.

8. The organic light-emitting composition according to claim 7, wherein The first host material includes one or more of the compounds having the structural formulae shown in Formulae H1-1 to H1-44 below:

9. The organic light-emitting composition according to any one of claims 6 to 8, characterized in that The dicyanobenzene-based compound includes one or more of the compounds having the structural formulae shown in Formulae Ph-2CN-1 to Ph-2CN-6 below: Y1, Y2, Y3, Y4, Y5, Y6, Y7, Y8, and Y9 are independently O or S; R s1 、R s2 、R s3 、R s4 、R s5 and R s6 are independently C6-C24 aryl or C12-C36 heteroaryl; R s7 ~R s39 independently is H, deuterium, C1-C6 alkyl, C1-C6 alkoxy or C6-C24 aryl; The alkyl, alkoxy, cycloalkyl, aryl, and heteroaryl are unsubstituted or optionally substituted with one or more substituents selected from the following: deuterium, halogen, -CN, C1-C12 alkyl, C1-C12 alkoxy, C1-C12 haloalkyl, C2-C6 alkenyl, C3-C10 cycloalkyl, C6-C14 aryl, and 5- to 18-membered heteroaryl; Optionally, R s1 , R s2 , R s3 , R s4 , R s5 and R s6 are independently selected from any one of the following groups: Optionally, R s7 ~R s39 is independently selected from any one of the following groups:

10. The organic light-emitting composition according to claim 9, characterized in that, The dicyanobenzene-based compound includes one or more of the compounds having the structural formulae shown in Formulae 2CN-1 to 2CN-60 below:

11. The organic light-emitting composition according to any one of claims 6 to 8 and 10, characterized in that, The phosphorescent compound containing metal Ir includes one or more of the compounds having the structural formulae shown in Formulae Ir-I to Ir-II below: R r1 ~R r22 Independently, it is hydrogen, deuterium, C1-C18 alkyl, deuterated C1-C18 alkyl, C6-C18 aryl, C6-C18 aryl substituted with at least one C1-C18 alkyl, wherein the dashed line represents that any two of the four included bonds that are separated from each other are double bonds; Optionally, R r1 ~R r22 forms a 6- to 20-membered fused ring or does not form a fused ring with the substituted ring, and the fused ring is substituted or unsubstituted by at least one C1-C18 alkyl group.

12. The organic light-emitting composition according to claim 11, characterized in that, The phosphorescent compound containing metal Ir includes one or more of the compounds having the structural formulae shown in Formulae Ir-1 to Ir-16 below:

13. An organic light-emitting ink material, characterized in that, It includes one or more of the spirofluorene-based organic compounds described in any one of Claims 1 to 5 and one or more of the organic light-emitting compositions described in any one of Claims 6 to 12, and a solvent system.

14. The organic light-emitting ink material according to claim 13, characterized in that, The solvent system includes a first solvent, a surface tension regulator, and a viscosity regulator; Optionally, the viscosity of the solvent system is 1 cps to 20 cps, and the surface tension is 20 to 60 dyne / cm; Optionally, the solvent system further includes a second solvent.

15. The organic light-emitting ink material according to claim 13, characterized in that, The solvent system has at least one of the following characteristics: (1) The first solvent is one or more of a liquid organic compound containing a benzene ring structure or a liquid naphthalene compound; Optionally, the weight percentage range of the first solvent in the solvent system is 60% to 98%; Optionally, the first solvent is a benzoate solvent. Further optionally, the first solvent is one or more of methyl benzoate, ethyl benzoate, ethyl p-methylbenzoate, isobutyl benzoate, 2-ethylhexyl benzoate, and ethyl p-methylbenzoate; (2) The second solvent is one or more of alcohols, ketones, ethers, esters, amides, and aromatic compounds; Optionally, the weight percentage range of the second solvent in the solvent system is 0.1% to 30%; Optionally, the second solvent is an aromatic hydrocarbon solvent. Further optionally, the second solvent is one or more of chlorobenzene, xylene, cyclohexylbenzene, 1-hexylbenzene, 1-hexylnaphthalene, 1-heptylbenzene, 1-octylbenzene, 1-decylbenzene, 4,4'-diethylbiphenyl, 3,4'-diisopropylbiphenyl, and 4,4'-diisopropylbiphenyl; (3) The surface tension regulator is one or more of a co-solvent, a surfactant, and a small molecule compound for regulating surface tension; the small molecule compound for regulating surface tension includes one or more of imidazole and its derivatives, phenol, and hydroquinone; Optionally, the weight percentage range of the surface tension regulator in the solvent system is 0.1% to 5%; Optionally, the surface tension regulator is one or more of cymene and hydroquinone; (4) The viscosity regulator is one or more of alcohols, ethers, esters, phenols, and amine compounds; Optionally, the weight percentage range of the viscosity regulator in the solvent system is 0.1% - 5%; Optionally, the viscosity regulator is one or more of benzyl benzoate and butyl stearate.

16. The organic light-emitting ink material according to any one of claims 13 to 15, characterized in that By weight percentage, the host material is 99.7% to 70.0%, the luminescent material is 0.3% to 30.0%, and the total concentration of the host material and the luminescent material in the organic light-emitting ink material is 5 mg / mL to 50 mg / mL; Optionally, in the host material, the weight ratio of the first host material to the second host material is 1:20 to 20:1; Optionally, the total concentration of the host material and the luminescent material in the organic light-emitting ink material is 10 mg / mL to 40 mg / mL, and further optionally 20 mg / mL to 40 mg / mL.

17. Use of the spirofluorene-based organic compound according to any one of claims 1 to 5, the organic light-emitting composition according to any one of claims 6 to 12, or the organic light-emitting ink material according to any one of claims 13 to 16 in the preparation of an organic electronic device.

18. An organic electronic device, characterized in that, It includes a functional layer, and the functional layer contains one or more of the spirofluorene organic compounds described in any one of claims 1 to 5 and the organic light-emitting composition described in any one of claims 6 to 12, or the functional layer is prepared from the organic light-emitting ink material described in any one of claims 13 to 16; Optionally, the preparation method is a solution method; further optionally, the solution method includes inkjet printing, letterpress printing, screen printing, dip coating, spin coating, blade coating, roller printing, reverse roller printing, plate printing, rotary printing, spraying, brush coating, pad printing or slot die coating.

19. The organic electronic device according to claim 18, wherein, The organic electronic device is an organic light-emitting diode, an organic solar cell, an organic field-effect transistor, an organic light-emitting field-effect transistor, an organic laser, an organic spintronic device, an organic sensor or an organic plasmonic emitting diode.

20. The organic electronic device according to claim 18 or 19, characterized in that, The organic electronic device includes a substrate and an anode layer, the functional layer, and a cathode layer formed in sequence on the substrate. The functional layer includes a light-emitting layer, and the light-emitting layer contains one or more of the spirofluorene organic compounds described in any one of claims 1 to 5 and the organic light-emitting composition described in any one of claims 6 to 12, or the light-emitting layer is prepared from the organic light-emitting ink material described in any one of claims 13 to 16; Optionally, the functional layer further includes one or more of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

21. A display device or a lighting device, characterized in that, It includes the organic electroluminescent device described in any one of claims 18 to 20.

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