Composition containing carbazole compound and compound

Abstract

The invention provides a composition containing a carbazole compound and a compound. The composition containing the carbazole compound comprises a first component and a second component, the first component is a carbazole compound, and the carbazole compound has a structure as shown in a formula I or a formula II; the second component comprises a compound A; the compound A is obtained by condensing any two adjacent carbon atoms on the ring A in a group shown in a formula I-A and a group shown in a formula I-B, and the compound A at least contains one deuterium atom. The composition containing the carbazole compound is designed, and the structure of the carbazole compound is further designed, so that the carbazole compound is suitable for being used as a main body material of a phosphorescent light-emitting layer of the organic electroluminescent device, and the organic electroluminescent device has relatively high current efficiency and relatively long service life.

Description

Technical Field

[0001] This invention belongs to the field of organic electroluminescent materials technology, specifically relating to a composition and compound containing carbazole compounds. Background Technology

[0002] The structure of an organic light-emitting diode (OLED) device specifically consists of an anode, a cathode, and an organic layer between them. To improve the efficiency and stability of OLED devices, the organic material layer comprises multiple layers with different materials, such as a hole injection layer (HIL), a hole transport layer (HTL), a hole blocking layer, an emissive layer, an electron transport layer (ETL), and an electron injection layer (EIL). Currently, organic light emission has become a mainstream display technology, and correspondingly, various novel OLED materials have been developed.

[0003] To meet the higher demands of people for OLED devices, there is an urgent need in the field to develop more types of materials to improve the performance of OLED devices in terms of current efficiency, lifetime, and other aspects. Summary of the Invention

[0004] To address the shortcomings of existing technologies, the present invention aims to provide a composition and compound containing carbazole compounds. The present invention designs the composition's structure and further designs the structures of the carbazole compounds and compound A to make them suitable as the main material for the phosphorescent layer of an organic electroluminescent device, thereby enabling the organic electroluminescent device to have high current efficiency and long lifespan.

[0005] To achieve this objective, the present invention adopts the following technical solution:

[0006] In a first aspect, the present invention provides a composition containing a carbazole compound, the composition comprising a first component and a second component;

[0007] The first component is a carbazole compound, which has the structure shown in Formula I or Formula II:

[0008]

[0009] In the compound of formula I, R1, R2, and R3 are each independently selected from hydrogen atoms or deuterium atoms, and at least one of R1, R2, and R3 is selected from deuterium atoms (-D).

[0010] In the compound of formula I, Ar is selected from any one of single bond, C6-C40 arylene, or C6-C30 heteroarylene;

[0011] In the compound of formula I, Ar1 and Ar2 are each independently selected from any one of H, C6-C40 aryl or C6-C30 heteroaryl;

[0012] In the compound of formula I, A1, A2, and A3 are each independently selected from N or CR, and at least one is selected from N; R is selected from any one of H, -CN, C6-C20 aryl or C1-C12 alkyl;

[0013] In the compound of formula I, a and b are each independently selected from 0 or 1, and at least one of a and b is selected from 1;

[0014] In the compound of formula II, R4, R5, R6, R7, and R8 are each independently selected from hydrogen atoms or deuterium atoms, and at least one of R4, R5, R6, R7, and R8 is selected from deuterium atoms (-D).

[0015] In the compound of formula II, Ar is selected from any one of single bond, C6-C40 arylene, or C6-C30 heteroarylene;

[0016] In the compound of formula II, Ar1 and Ar2 are each independently selected from any one of H, C6-C40 aryl or C6-C30 heteroaryl;

[0017] In the compound of formula II, A1, A2, and A3 are each independently selected from N or CR, and at least one is selected from N; R is selected from any one of H, -CN, C6-C20 aryl or C1-C12 alkyl;

[0018] In the compound of formula II, a and b are each independently selected from 0 or 1, and at least one of a and b is selected from 1;

[0019] In compounds of formula I and formula II, the hydrogen atoms can be independently substituted by at least one of deuterium (-D), -F, -CN, C6-C20 aryl, triphenylmethyl, triphenylsilyl, C1-C12 alkyl or C1-C12 alkoxy.

[0020] In the compound of formula I / compound II provided by this invention, one side is a nitrogen-containing heterocycle and the other side is a carbazole-like structure. The HOMO molecule is mainly distributed on the carbazole-like structure side, and the LUMO molecule is mainly distributed on the nitrogen-containing heterocycle side. When used as the main material of the light-emitting layer, the compound of formula I / compound II is in an excited state. At this time, intramolecular electron transfer or energy transfer occurs, which will affect the luminous efficiency of the device. Therefore, how to block the energy transfer or electron transfer between the carbazole-like structure side and the nitrogen-containing heterocycle side is a problem that needs to be considered.

[0021] The applicant discovered that by replacing the H atoms on the benzene / naphthalene ring between the carbazole structure and the nitrogen heterocycle with D atoms, energy or electron transfer between the carbazole structure side and the nitrogen heterocycle side can be effectively blocked, thereby improving the luminous efficiency of the device. Simultaneously, the device lifetime is also improved.

[0022] In this invention, the structure of carbazole compounds is designed to be suitable as the main material for the phosphorescent light-emitting layer of organic electroluminescent devices, thereby enabling the organic electroluminescent devices to have high current efficiency and long lifespan.

[0023] In this invention, C6-C40 can be C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36 or C40, etc.

[0024] C6-C30 can be C6, C8, C10, C12, C16, C20, C24, C28, or C30, etc.

[0025] C6-C20 can be C6, C8, C10, C12, C16, or C20, etc.

[0026] C1-C12 can be C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11 or C12.

[0027] It should be noted that in this invention, "-D" represents a deuterium atom, and the same applies below.

[0028] The following are preferred technical solutions of the present invention, but are not intended to limit the technical solutions provided by the present invention. The purpose and beneficial effects of the present invention can be better achieved and realized through the following preferred technical solutions.

[0029] As a preferred embodiment of the present invention, the C6-C40 arylene group is selected from phenylene, biphenylene, terphenylene, naphthylene, anthracene, phenanthrene, fluorene, benzo[a]fluorene, dibenzo[a]fluorene, naphthylene, pyrene, perylene, spirofluorene, phenylenetriene, fluorenylene, hydrogenated benzo[a]anthrayl, indene, benzo[a]indene, dibenzo[a]indene, naphthylene, and tetraphenylmethane. Or any one or a combination of at least two of benzo[a]naphtho[b]fluorene.

[0030] As a preferred embodiment of the present invention, the C6-C30 heteroaryl group is selected from any one of imidazolyl, dibenzothiophene, naphthobenzofuranyl, naphthobenzothiophene, dibenzofuranyl, dibenzothiophene, or imidazolyl.

[0031] As a preferred embodiment of the present invention, the C6-C40 aryl group is selected from any one or a combination of at least two of the following: phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, fluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, naphthyl, pyrene, perylene, spirofluorenyl, triphenylene, fluoranyl, hydrogenated benzo[a]anthrayl, ind[a]fluorenyl, benzo[a]ind[a]fluorenyl, dibenzo[a]ind[a]fluorenyl, naphthyl, tetraphenylmethane, or benzo[a]naphthyl.

[0032] As a preferred embodiment of the present invention, the C6-C30 heteroaryl group is selected from any one or a combination of at least two of carbazolyl, dibenzothiophenel, dibenzofuranyl, naphthobenzofuranyl, naphthobenzothiophenel, dinaphthofuranyl, and dinaphthothiophenel.

[0033] Preferably, the C6-C20 aryl group is selected from any one of phenyl, naphthyl, biphenyl, anthracene, phenanthryl, fluorenyl, triphenylene, or fluoranthracene.

[0034] Preferably, the C1-C12 alkyl group is selected from any one of methyl, ethyl, propyl, n-butyl, tert-butyl, cyclopentyl, cyclohexyl, octyl, and adamantyl.

[0035] Preferably, the C1-C12 alkoxy group is selected from any one of methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, and octoxy.

[0036] As a preferred embodiment of the present invention, in the compounds of Formula I and Formula II, the Ar is independently selected from any one of single bond, phenylene, carbazolyl, biphenylene, fluorene, naphthylene, triphenylene, fluorenylene, indofluorene, dibenzothiophene, naphthanobenzofuranyl, naphthanobenzothiophene, or carbazolyl.

[0037] Preferably, in the compounds of Formula I and Formula II, Ar is independently selected from at least one of single bond, phenylene, carbazolyl, naphthylene, 9,9-dimethylfluorenyl, dibenzothiophene, dibenzofuranyl or biphenylene, and more preferably any one of single bond, phenylene, biphenylene or carbazolyl.

[0038] As a preferred embodiment of the present invention, in the compounds of Formula I and Formula II, Ar1 and Ar2 are each independently selected from any one or a combination of at least two of H, phenyl, carbazolyl, biphenyl, 9,9-dimethylfluorenyl, naphthyl, triphenylene, fluoranyl, indenefluorenyl, dibenzofuranyl, dibenzothiophene, naphthobenzofuranyl or naphthobenzothiophene.

[0039] Preferably, in the compounds of Formula I and Formula II, Ar1 and Ar2 are each independently selected from at least one of H, phenyl, carbazolyl, naphthyl, 9,9-dimethylfluorenyl, dibenzothiophene, biphenyl, dibenzofuranyl, triphenylene, or fluoranyl, and more preferably at least one of phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophene, or carbazolyl.

[0040] As a preferred embodiment of the present invention, any one of A1, A2, and A3 is selected from N, the other two are CR, and R is selected from H or -CN.

[0041] Preferably, any two of A1, A2, and A3 are selected from N, the other is CR, and R is selected from H or -CN.

[0042] Preferably, A1, A2, and A3 are all selected from N.

[0043] Preferably, in Formula I, R1, R2, and R3 are all selected from deuterium atoms.

[0044] Preferably, in Formula II, R4, R5, R6, R7, and R8 are all selected from deuterium atoms.

[0045] As a preferred embodiment of the present invention, the hydrogen atoms in the compounds of Formula I and Formula II can each be independently substituted by at least one of -D, -F, -CN, phenyl, naphthyl, biphenyl, triphenylmethyl, triphenylsilyl, methyl, ethyl, propyl, butyl, methoxy, ethoxy, propoxy, or butoxy.

[0046] Preferably, the hydrogen atoms in the compounds of Formula I and Formula II can each be independently substituted by at least one of -D, -F, -CN, phenyl, naphthyl, methyl, ethyl, tert-butylmethoxy, ethoxy, and propoxy.

[0047] As a preferred embodiment of the present invention, the carbazole compound is selected from any one of the following substituted or unsubstituted compounds:

[0048]

[0049]

[0050]

[0051]

[0052] The substitution refers to the independent substitution of each hydrogen atom in the aforementioned carbazole compounds by a deuterium atom. Preferably, the carbazole compounds are selected from any one of the following compounds:

[0053]

[0054] As a preferred embodiment of the present invention, the second component includes compound A;

[0055] Compound A is obtained by fusion of a group with the structure shown in Formula IA and any two adjacent carbon atoms on ring A in the group with the structure shown in Formula IB:

[0056]

[0057] Where * represents a fusion site;

[0058] X is selected from O, S, R 301 R 302 Each is independently selected from C1-C6 alkyl, C6-C30 aryl, or C6-C20 heteroaryl, and R 301 R 302 A ring can be formed by connecting with a single key, R 303 Selected from C6-C30 aryl or C6-C20 heteroaryl, with dashed lines indicating connection sites;

[0059] Ar 22 Selected from C6-C30 aryl or C6-C20 heteroaryl;

[0060] In compound A, each hydrogen atom can be independently substituted by at least one of -F, -D, -CN, C6-C20 aryl, C1-C6 alkyl, and C1-C6 alkoxy, and at least one hydrogen atom in compound A is substituted by -D.

[0061] In compound A, C6-C30 can be C6, C10, C12, C18, C24, or C30, etc.

[0062] The C6-C20 can be C6, C10, C12, C18, or C20, etc.

[0063] The C1-C6 can be C1, C2, C3, C4, C5 or C6.

[0064] As a preferred embodiment of the present invention, in compound A, the R 303 Ar 22Each group is independently selected from any one or a combination of two of the following substituted or unsubstituted groups: phenyl, biphenyl, naphthyl, anthracene, phenanthrene, fluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, triphenylene, fluoranyl, pyrene, perylene, spirofluorenyl, dibenzofuranyl, dibenzothiophene, naphthobenzofuran, naphthobenzothiophene, dinaphthofuran, dinaphthothiophene, hydrogenated benzene Anthrayl, indo-carbazolyl, indo-carbazolyl, terphenyl, tetraphenyl, imidazolyl, benzimidazolyl, pyridyl, pyrimidinyl, piperazine, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzoquinoxalinyl, benzoquinoxalinyl, N-phenanthroline, diazanthroline, carbazolyl, benzo-carbazolyl, naphtho-carbazolyl, dibenzo-carbazolyl, triazine;

[0065] The substituents are each independently selected from at least one of C1-C12 (e.g., C1, C2, C5, C6, C8, C10, or C12), C1-C12 (e.g., C1, C2, C5, C6, C8, C10, or C12), and C6-C12 (e.g., C6, C7, C8, C9, C10, C11, or C12) aryl groups.

[0066] As a preferred technical solution of the present invention, the R 303 Ar 22 Each group is independently selected from any one or a combination of two of the following substituted or unsubstituted groups: phenyl, biphenyl, naphthyl, phenanthryl, anthracene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl, dibenzofuranyl, dibenzothiopheneyl, triphenylene, fluorenyl, carbazoleyl, benzofluorenyl;

[0067] The substituent is selected from at least one of methyl, ethyl, tert-butyl, adamantyl, cyclohexyl, cyclopentyl, 1-methylcyclopentyl, 1-methylcyclohexyl, methoxy, phenyl, biphenyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophene, or naphthyl.

[0068] Preferably, X is selected from O and S.

[0069] Preferably, the R 301 R 302 Each is independently selected from methyl or phenyl.

[0070] Preferably, the R 303 Selected from phenyl, diphenyl, or triphenyl.

[0071] Preferably, the Ar 22 Selected from diphenyl, triphenyl, or tetraphenyl.

[0072] Preferably, the R 303 The Ar is phenyl.22 Selected from diphenyl, triphenyl, or tetraphenyl.

[0073] Preferably, the R 303 It is a diphenyl group, and the Ar is... 22 Selected from diphenyl or triphenyl.

[0074] As a preferred embodiment of the present invention, in compound A, at least one hydrogen atom on ring A, ring B or ring C is replaced by -D.

[0075] Preferably, Ar in compound A 22 R 301 R 302 Or R 303 At least one hydrogen atom on a substituent is replaced by -D.

[0076] As a preferred embodiment of the present invention, compound A has a structure as shown in formulas I-1 to I-30: and each of the compounds shown in formulas I-1 to I-30 can be independently substituted by at least one of -F, -D, -CN, C6-C20 (e.g., C6, C10, C12, C18 or C20, etc.) aryl, C1-C6 (e.g., C1, C2, C3, C4, C5 or C6) alkyl, and C1-C6 (e.g., C1, C2, C3, C4, C5 or C6) alkoxy.

[0077]

[0078] Among them, R 303 Ar 22 It has the same definition as above.

[0079] As a preferred embodiment of the present invention, compound A is selected from any one of the following compounds, and at least one hydrogen atom in the following compounds is substituted with -D:

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095] Preferably, compound A is selected from any one of the following compounds, and at least one hydrogen atom in the following compounds is substituted with -D:

[0096]

[0097]

[0098]

[0099] Preferably, compound A is selected from any one of the following compounds:

[0100]

[0101]

[0102] It should be noted that there are no special restrictions on the preparation methods of the above compounds in this invention, and commonly used preparation methods in the art are applicable.

[0103] In a second aspect, the present invention provides a compound comprising compound H-601DE, compound H-601D, compound H-602DE, and compound H-603DE:

[0104]

[0105] Thirdly, the present invention provides an organic electroluminescent device, the organic electroluminescent device comprising an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode;

[0106] The organic thin film layer material includes the composition as described in the first aspect or the compound as described in the second aspect.

[0107] As a preferred embodiment of the present invention, the organic thin film layer includes a light-emitting layer, and the main material of the light-emitting layer includes the composition as described in the first aspect or the compound as described in the second aspect.

[0108] Preferably, the light-emitting layer is a phosphorescent light-emitting layer.

[0109] As a preferred embodiment of the present invention, the organic electroluminescent device is a green organic electroluminescent device.

[0110] In this invention, the light-emitting layer comprises a host material and a dopant material, wherein the dopant material is also called a dye or a phosphorescent material. The host material of the light-emitting layer can be a single compound or a mixture of two or more compounds.

[0111] The light-emitting layer includes a phosphorescent light-emitting layer, which includes a green phosphorescent light-emitting layer, a red phosphorescent light-emitting layer, a yellow phosphorescent light-emitting layer, and a blue phosphorescent light-emitting layer.

[0112] The volume percentage of the main material in the phosphorescent luminescent layer is 60% to 99.9% (e.g., it can be 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, 98%, or 99.9%), preferably 70% to 99.5%, and more preferably 85% to 95%.

[0113] In this invention, the doping material of the light-emitting layer can be a phosphorescent material, also known as a triplet luminescent material, which refers to the light emitted by a substance from a triplet excited state. The specific selection of phosphorescent materials in this invention is not particularly limited; commonly used doping materials for the light-emitting layer in this field are applicable, including but not limited to compounds having the structure shown in the formula PD.

[0114]

[0115] Wherein, M is selected from any one of Ir, Pt, Pd, Os, Ti, Zr, Hf, Eu, Tb, Tm, Cu or Au;

[0116] Y1-Y4 are each independently selected from carbon or nitrogen;

[0117] Y1 and Y2 can be connected by a single key or a double key, and Y3 and Y4 can be connected by a single key or a double key.

[0118] Cy1 and Cy2 are each independently selected from any one of phenyl, naphthyl, fluorenyl, spirofluorenyl, indyl, pyrroleyl, thiopheneyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, benzimidazolyl, benzofuranyl, benzothiopheneyl, isobenzothiopheneyl, benzimidazolyl, benzozolyl, triazolyl, tetrazolyl, diazolyl, triazinyl, dibenzothiopheneyl, and n-hexacarbazolyl, wherein Cy1 and Cy2 may optionally be linked to each other via a single bond or an organic linking group;

[0119] Any two or more ligands of M can be connected by single or double bonds, or by O or S bridging, or by any chemical group or chemical structure to form a structure that conforms to chemical principles.

[0120] R 91 and R 92Each group is independently selected from -H, -D, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group, carboxylate group, sulfonic acid group, sulfonate group, phosphate group, phosphate group, -SF5, substituted or unsubstituted C1-C60 (e.g., can be C1, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55, or C60, etc.) alkyl, substituted or unsubstituted C2-C6. 0 (e.g., can be C2, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55, or C60, etc.) alkenyl, substituted or unsubstituted C2-C60 (e.g., can be C2, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55, or C60, etc.) alkynyl, substituted or unsubstituted C1-C60 (e.g., can be C1, C5, C10, C15, C20, C40, C50, C55, C60, etc.) alkyne, substituted or unsubstituted C1-C60 (e.g., can be C1, C5, C10, C15, C20, C50, C10, C15, C20, C1 ... 25. alkoxy, substituted or unsubstituted C2-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, or C10), heterocyclic alkyl, substituted or unsubstituted C6-C60 (e.g., C6, C12, C15, C18, C24, C30, C32, C36, C40, C42, C54, or C60), aryl, substituted or unsubstituted C6-C60 (… For example, it can be any one of the following: aryloxy group (C6, C12, C15, C18, C24, C30, C32, C36, C40, C42, C54 or C60, etc.), substituted or unsubstituted C6-C60 (e.g., it can be C6, C12, C15, C18, C24, C30, C32, C36, C40, C42, C54 or C60, etc.), substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or substituted or unsubstituted monovalent non-aromatic fused heterocyclic group.

[0121] a1 and a2 are each independent integers selected from 1 to 5, for example, they can be 1, 2, 3, 4 or 5;

[0122] b is an integer selected from 0 to 4, for example, it can be 0, 1, 2, 3 or 4;

[0123] a is selected from 1, 2, or 3;

[0124] L1 can be a monovalent organic ligand, a divalent organic ligand, or a trivalent organic ligand.

[0125] Preferably, the PD compound is selected from any one of the following compounds:

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132] In this invention, the organic thin film layer includes a hole layer, which comprises a hole injection layer, a hole transport layer, and an electron blocking layer.

[0133] The hole injection layer material includes a P-type dopant. A P-type dopant is a material that coexists with the hole injection layer material in the OLED device, oxidizing the hole injection layer material and thus acting as an electron acceptor to promote the movement of holes from the hole injection layer to the anode. In this invention, the difference between the absolute value of the LUMO of the P-type dopant and the absolute value of the HOMO of the hole layer material is greater than -0.2V, preferably greater than -0.1eV, more preferably greater than 0eV, more preferably greater than 0.1eV, and more preferably greater than 0.2eV.

[0134] The P-type dopant exists in the hole injection layer at a volume percentage of 1% to 10% (e.g., 1%, 2%, 4%, 6%, 8%, or 10%). In this invention, no particular limitation is made on the type of P-type dopant; exemplarily, compounds D-1 to D-13 disclosed in CN113728453A or compounds HI-1 to HI-9 as described below can be used.

[0135]

[0136]

[0137] In this invention, the hole layer material (including a hole injection layer, a hole transport layer, and an electron blocking layer) has the structure shown in the following formula HT-GH4:

[0138]

[0139] Among them, L 41 Selected from single-bonded, C6-C40 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36, or C40, etc.) aryl, and C6-C20 (e.g., C6, C8, C10, C12, C16, or C20, etc.) heteroaryl;

[0140] Ar 41 Ar42 Each is independently selected from C6-C40 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36, or C40, etc.) aryl and C6-C20 (e.g., C6, C8, C10, C12, C16, or C20, etc.) heteroaryl;

[0141] X is selected from CR 41 R 42 Or NR 43 , where R 41 R 42 R 43 Each is independently selected from substituted or unsubstituted phenyl groups (the substituents are selected from C1-C6 (e.g., C1, C2, C3, C4, C5, or C6) alkyl, C1-C6 (e.g., C1, C2, C3, C4, C5, or C6) alkoxy, naphthyl, triphenylene, fluoranyl, 9,9-dimethylfluorenyl, biphenyl, substituted or unsubstituted group (the substituent is phenyl), substituted or unsubstituted dibenzothiophene (the substituent is phenyl), substituted thiophene, C1-C6 (e.g., C1, C2, C3, C4, C5, or C6) alkyl groups, R 41 R 42 They can be connected into a ring using a single key.

[0142] The HT-GH4 compound is selected from any one of the following compounds:

[0143]

[0144]

[0145]

[0146] In this invention, the hole layer material (including a hole injection layer, a hole transport layer, and an electron blocking layer) further includes a compound having a structure as shown in Formula IA or a compound having a structure as shown in Formula IB:

[0147]

[0148] Wherein, L is selected from any one of C6-C40 (e.g., it can be C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36 or C40, etc.) arylene, dibenzofuranyl or dibenzothiophene group;

[0149] m is selected from an integer between 0 and 4 (for example, it can be 0, 1, 2, 3 or 4), and n is selected from 0 or 1;

[0150] Ar is selected from any one of triphenylene, fluorene anthracene, dibenzofuranyl or dibenzothiophene;

[0151] Ar1 and Ar2 are each independently selected from any one of aryl, dibenzofuran, or dibenzothiophene groups containing C6-C40 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36, or C40, etc.);

[0152] Ar1 and Ar, Ar2 and Ar, and Ar1 and Ar2 can be independently connected or bridged by single bonds, O, S, CR1R2, NR.

[0153] R, R1, and R2 are each independently selected from any one of the following: C1-C20 (e.g., C1, C2, C4, C6, C8, C10, C12, C14, C16, C18, or C20), alkyl, C6-C40 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36, or C40), aryl, dibenzofuranyl, or dibenzothiopheneyl.

[0154] In compounds of formula IB and formula IA, the H can be independently replaced by at least one of -F, -CN, -D (deuterium atom), C1-C6 alkyl, C1-C6 alkoxy, phenyl, biphenyl, naphthyl, phenanthryl, anthracene, fluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, triphenylene, fluoranyl, pyrene, perylene, spirofluorenyl, indo[a]fluorenyl, or hydrogenated benzo[a]anthryl.

[0155] Preferably, the Ar is fluoreneanthracene, where m+n>1.

[0156] Preferably, the H in the compounds of formula IB and formula IA can be replaced by at least one of -F, -CN, -D, C1-C3 alkyl (e.g., methyl, ethyl, or propyl), C1-C3 alkoxy (e.g., methoxy, ethoxy, or propoxy), phenyl, biphenyl, triphenylene, and fluoranthyl.

[0157] Preferably, L, Ar1, and Ar2 are each independently selected from at least one of phenyl, biphenyl, naphthyl, phenanthryl, anthracene, fluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, triphenylene, fluoranyl, pyrene, perylene, spirofluorenyl, indo[a]fluorenyl, or hydrogenated benzo[a]anthryl.

[0158] Preferably, the compound of formula IB is selected from any one of the following compounds 1-112:

[0159]

[0160] In the OLED device provided by this invention, the hole layer material, in addition to the compounds described in formula HT-GH4, formula IB, and formula IA, may also include conventional hole materials in the art, without particular limitation. Exemplarily, it includes, but is not limited to, triarylamine compounds or carbazole compounds. Preferably, triarylamine compounds or carbazole compounds containing three or more nitrogen atoms are preferred because they have a higher HOMO (lower absolute value) and are more suitable as hole injection layer materials. Triarylamine compounds or carbazole compounds containing two or one nitrogen atom can be used as hole transport layer materials. Some compounds or carbazole compounds containing one nitrogen atom, if they have a high LUMO, can also be used as electron blocking layer materials.

[0161] The triaryl amine compound or carbazole compound is used as the hole layer material, and the hole layer material includes the following structure:

[0162]

[0163] Among them, Ar 601 ~Ar 609 Each is independently selected from any one of the following: substituted or unsubstituted C6-C40 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36, or C40, etc.) aryl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted naphthobenzofuran, substituted or unsubstituted naphthobenzothiophene, substituted or unsubstituted dinaphthofuran, substituted or unsubstituted dinaphthothiophene;

[0164] And Ar 601 ~Ar 609 Ar atoms that are adjacent to or connected to the same N atom 601 ~Ar 609 It can be connected via a single key or via O, S, CR 701 R 702 NR 703 bridging;

[0165] R 701 R 702 R 703 Selected from C6-C40 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36, or C40, etc.) aryl, C6-C20 (e.g., C6, C8, C10, C12, C16, or C20, etc.) heteroaryl, C1-C6 (e.g., C1, C2, C3, C4, C5, or C6) alkyl, and R 701 R 702It can be connected with a single button.

[0166] Hole blocking layers (HBLs) can confine holes and / or excitons within the emissive layer to improve device current efficiency and lifetime. Compared to emissive layer materials closest to the HBL interface, HBL materials exhibit lower HOMO (larger absolute values) and / or higher triplet energies.

[0167] An electron transport layer (ETL) may comprise a material capable of transporting electrons. The ETL may be intrinsic (undoped) or doped, and doping can be used to enhance conductivity. In this invention, there are no particular limitations on the ETL material; any metal complex or organic compound can be used, as long as it can transport electrons. Generally, electron transport layer materials contain at least one of the following structural segments: pyridine, pyrimidine, triazine, benzimidazole, benzoxazole, benzothiazole, N-naphthalene, N-phenanthion, N-carbazole, and N-dibenzothiophene.

[0168] In this invention, no special restrictions are placed on the electron transport layer material, which includes, but is not limited to, the following:

[0169]

[0170] In this invention, the cathode material is a metal with low work function (e.g., alkaline earth metals, alkali metals, main group metals, or lanthanides (e.g., Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.)), a metal alloy composed of multiple metals (an alloy composed of alkali metals or alkaline earth metals and silver, such as an alloy composed of magnesium and silver), or a multilayer structure. If the cathode material is a multilayer structure, in addition to the metals mentioned above, other metals with relatively high work function can also be used, such as Ag or Al. In this case, combinations of the metals are typically used, such as Ca / Ag, Mg / Ag, or Ba / Ag.

[0171] Alternatively, a thin interlayer of material with a high dielectric constant can be introduced between the metal cathode and the organic semiconductor to form a multilayer structure; the material with a high dielectric constant can also be called an electron injection material, and can be an alkali metal or alkaline earth metal fluoride, as well as the corresponding oxide or carbonate (e.g., LiF, Li2O, BaF2, MgO, NaF, CsF, Cs2CO3, etc.) or lithium quinoline (LiQ).

[0172] Compared with the prior art, the present invention has the following beneficial effects:

[0173] In the first component of the composition provided by this invention, one side of the compound of formula I / compound II is a nitrogen-containing heterocycle, and the other side is a carbazole-like structure. The HOMO molecule is mainly distributed on the carbazole-like structure side, and the LUMO molecule is mainly distributed on the nitrogen-containing heterocycle side. When used as the main material of the light-emitting layer, the compound of formula I / compound II is in an excited state. At this time, intramolecular electron transfer or energy transfer occurs, which will affect the luminous efficiency of the device. Therefore, how to block the energy transfer or electron transfer between the carbazole-like structure side and the nitrogen-containing heterocycle side is a problem that needs to be considered.

[0174] The applicant discovered that by replacing the H atoms on the benzene / naphthalene ring between the carbazole structure and the nitrogen heterocycle with D atoms, energy or electron transfer between the carbazole structure side and the nitrogen heterocycle side can be effectively blocked, thereby improving the luminous efficiency of the device. Simultaneously, the device lifetime is also improved.

[0175] The second component of the composition provided by this invention is compound A, which is obtained by fusion of a group with the structure shown in formula IA and any two adjacent carbon atoms on ring A in the group with the structure shown in formula IB. The resulting structure is a large conjugated group with good planarity and a high electron cloud density distribution. Furthermore, the substitution of H atoms with D atoms at different positions in the second component has different effects on improving the voltage, efficiency, and lifetime performance of the device.

[0176] The composition of the first and second components has a suitable energy level structure and excited state stability. The two components work synergistically to improve the efficiency and lifespan of the device, while reducing the device voltage. Detailed Implementation

[0177] To facilitate understanding of the present invention, the following embodiments are provided. Those skilled in the art should understand that these embodiments are merely illustrative and should not be construed as limiting the scope of the invention.

[0178] Synthesis Example 1: Synthesis of H-601DE

[0179] This synthetic embodiment provides the synthesis of H-601DE, and the synthesis method is as follows:

[0180]

[0181] (1) Synthesis of intermediate H-601DE-1

[0182] Under nitrogen protection, dry toluene (50 mL), intermediate H-601DE-2 (2.7 g), 4-bromobiphenyl (2.3 g), Pd(dba)2 (bis(dibenzylacetone palladium, 0.0575 g, 0.0001 mol), a 10% (w / w) solution of tri-tert-butylphosphine toluene (0.4 g of tri-tert-butylphosphine solution, 0.0002 mol of tri-tert-butylphosphine), and sodium tert-butoxide (1.44 g, 0.015 mol) were added to a three-necked flask. The mixture was heated to reflux and reacted for 8 h. After cooling to room temperature, water was added to separate the contents. The organic layer was then washed with water until neutral, dried with magnesium sulfate, filtered to remove magnesium sulfate, concentrated to dryness, and separated by silica gel column chromatography. The mixture was eluted with a solvent of petroleum ether:ethyl acetate = 20:1 (v / v) to obtain intermediate H-601DE-1 (2.9 g).

[0183] Mass spectrometry analysis of intermediate H-601DE-1 revealed a mass-to-charge ratio (m / z) of 418.23.

[0184] (2) Synthesis of compound H-601DE

[0185] The compound H-601DE was prepared by referring to the synthesis of intermediate H-601DE-1.

[0186] Mass spectrometry analysis of compound H-601DE yielded a mass-to-charge ratio (m / z) of 570.29.

[0187] Synthesis Example 2: Synthesis of H-602DE

[0188] This synthetic example provides the synthesis of H-602DE, and the synthesis method is as follows:

[0189]

[0190] Under nitrogen protection, dry toluene (80 mL), intermediate H-601DE-2 (2.7 g), 4-bromobiphenyl (4.6 g), Pd(dba)2 (bis(dibenzylacetone)palladium, 0.0575 g, 0.0001 mol), a 10% (w / w) solution of tri-tert-butylphosphine in toluene (0.4 g of tri-tert-butylphosphine solution, 0.0002 mol of tri-tert-butylphosphine), and sodium tert-butoxide (1.44 g, 0.015 mol) were added to a three-necked flask. The mixture was heated to reflux and reacted for 24 h. After cooling to room temperature, water was added to separate the contents. The organic layer was then washed with water until neutral, dried with magnesium sulfate, filtered to remove magnesium sulfate, concentrated to dryness, and separated by silica gel column chromatography. The solution was eluted with a solvent of petroleum ether:ethyl acetate = 20:1 (v / v) to give compound H-602DE (4.7 g).

[0191] Mass spectrometry analysis of intermediate H-602DE showed a mass-to-charge ratio (m / z) of 570.29.

[0192] Synthesis Example 3: Synthesis of H-603DE

[0193] This synthetic example provides the synthesis of H-603DE, and the synthesis method is as follows:

[0194]

[0195] Following the synthesis of intermediate H-601DE-1, compound H-603DE was prepared.

[0196] Mass spectrometry analysis of compound H-603DE yielded a mass-to-charge ratio (m / z) of 646.32.

[0197] Synthesis of H-601D in Example 4

[0198] This synthetic embodiment provides the synthesis of H-601D, and the synthesis method is as follows:

[0199]

[0200] (1) Synthesis of intermediate H-601D-1

[0201] Compound H-601D-1 was prepared by referring to the synthesis of intermediate H-601DE-1.

[0202] Mass spectrometry analysis of compound H-601D-1 yielded a mass-to-charge ratio (m / z) of 413.19.

[0203] (2) Synthesis of compound H-601D

[0204] Compound H-601D was prepared by referring to the synthesis of intermediate H-601DE-1.

[0205] Mass spectrometry analysis of compound H-601D yielded a mass-to-charge ratio (m / z) of 570.29.

[0206] The specific structures of some of the compounds used in the following application examples and comparative application examples of this invention are as follows:

[0207]

[0208]

[0209] Application Example 1

[0210] This application example provides a green organic electroluminescent device, using the composition provided by the present invention as the host material for the light-emitting layer. The structure of the green organic electroluminescent device is as follows:

[0211] ITO / HT-1: HI-2[5%](100nm) / HT-1(30nm) / EB-2(20nm) / Main material: PGD-1[5%](35nm) / ETL-1(25nm) / LiF(0.5nm) / Al(150nm).

[0212] The fabrication method of the green organic electroluminescent device is as follows:

[0213] The material was placed inside a vacuum chamber, and the vacuum was evacuated to 1×10⁻⁶. -5 ~1×10 -6 Pa is sequentially vacuum-deposited onto a cleaned ITO substrate to fabricate OLED devices.

[0214] PGD-1 [5%] refers to the dye doping ratio, i.e., the volume ratio of the host material to the dye PGD-1 is 95:5. The host material consists of two components, and their volume ratio is 1:1. HT-1:HI-2 [5%] refers to the ratio of P-type dopant, i.e., the volume ratio of hole material HT-1 to P-type dopant HI-2 is 95:5. HT-1 is the hole transport material; HT-1:HI-2 [5%] is used as the hole injection layer, and EB-2 is the electron blocking layer.

[0215] The main materials of the light-emitting layer of the green organic electroluminescent device provided in this application example are compound P1 and H-601DE, and the volume ratio of the two is 5:5.

[0216] Application Example 2-6, Comparison with Application Example 1-3

[0217] Application Examples 2-6 and Comparative Application Examples 1-3 each provide a green organic electroluminescent device. The only difference from Application Example 1 is that the main material of the light-emitting layer is replaced with other compounds (see Table 1 below). The other preparation steps and conditions are the same as in Application Example 1.

[0218] The luminance, current efficiency, and LT95 of the organic electroluminescent devices provided above were tested. The voltage and current efficiency were measured at a luminance of 1000 cd / m². 2 The corresponding value, LT95, refers to maintaining an initial device current density of 10 mA / cm². 2 The time required for the device efficiency to drop to 95% of the efficiency corresponding to the initial current density, while remaining constant, is the time. The drive voltage, current efficiency, and LT95 are relative values. Specific test results are shown in Table 1 below:

[0219] Table 1

[0220] Main material 1 Main material 2 <![CDATA[Brightness / (cd / m 2 )]]> Drive voltage Current efficiency LT95 Application Example 1 P1 H-601DE 1000 1 1 1 Application Example 2 P1 H-601D 1000 0.94 1.03 0.91 Application Example 3 P1 H-602DE 1000 / 1.16 / Application Example 4 P1 H-603DE 1000 / / 1.08 Application Example 5 P2 H-601DE 1000 / / 1.05 Application Example 6 P12 H-601DE 1000 / 0.96 1 Comparative Application Example 1 P1 H-601 1000 1.03 0.96 0.88 Comparative Application Example 2 D1 H-601DE 1000 1.04 0.94 0.80 Comparative Application Example 3 D3 H-601DE 1000 1.06 0.92 0.72

[0221] The " / " indicates that this data is not available.

[0222] A comparison of Application Examples 1 and 2 shows that when hydrogen atoms on rings A, B, and C in compound A are deuterated, the lifetime of the prepared organic electroluminescent device is improved. However, because the electron cloud density of rings A, B, and C is relatively high, deuteration affects the electron cloud distribution of rings A, B, and C, leading to a decrease in device voltage and efficiency. In compound A, X and Ar... 22 Replacing some hydrogen atoms with deuterium atoms can improve the driving voltage and current efficiency of organic electroluminescent devices, but has little effect on improving lifetime.

[0223] As can be seen from the comparison between Application Examples 1-2 and Comparative Application Example 1, the presence of deuterium atoms in compound A improves the lifetime of organic electroluminescent devices. At the same time, compound A containing deuterium atoms, as host material 2, can better combine and synergize with host material 1, and the driving voltage and current efficiency of the prepared organic electroluminescent devices are also improved.

[0224] As can be seen from Application Example 3, the organic electroluminescent device prepared by using compound H-602DE as the host material 2 has a high current efficiency.

[0225] As can be seen from Application Example 4, the organic electroluminescent device prepared by using compound H-603DE as the host material 2 has a better lifetime.

[0226] As can be seen from Application Example 6 and Application Example 1, the increased deuteration rate in Formula I compounds does not significantly improve the performance of organic electroluminescent devices.

[0227] In summary, by designing the composition of the composition and further designing the structure of carbazole compounds and compound A, this invention makes them suitable as the main material for the phosphorescent light-emitting layer of organic electroluminescent devices, thereby enabling the organic electroluminescent devices to have high current efficiency and long lifespan.

[0228] The applicant declares that the detailed process flow of this invention is illustrated by the above embodiments, but this invention is not limited to the above detailed process flow, that is, it does not mean that this invention must rely on the above detailed process flow to be implemented. Those skilled in the art should understand that any improvements to this invention, equivalent substitutions of raw materials for the product of this invention, addition of auxiliary components, and selection of specific methods, etc., all fall within the protection scope and disclosure scope of this invention.

Claims

1. A composition containing a carbazole compound, characterized in that, The composition containing carbazole compounds comprises a first component and a second component; The first component is a carbazole compound, which has the structure shown in Formula I or Formula II: In the compound of formula I, R1, R2, and R3 are each independently selected from hydrogen atoms or deuterium atoms, and at least one of R1, R2, and R3 is selected from deuterium atoms; In the compound of formula I, Ar is selected from any one of single bond, C6-C40 arylene, or C6-C30 heteroarylene; In the compound of formula I, Ar1 and Ar2 are each independently selected from any one of H, C6-C40 aryl or C6-C30 heteroaryl; In the compound of formula I, A1, A2, and A3 are each independently selected from N or CR, and at least one is selected from N; R is selected from any one of H, -CN, C6-C20 aryl or C1-C12 alkyl; In the compound of formula I, a and b are each independently selected from 0 or 1, and at least one of a and b is selected from 1; In the compound of formula II, R4, R5, R6, R7, and R8 are each independently selected from hydrogen atoms or deuterium atoms, and at least one of R4, R5, R6, R7, and R8 is selected from deuterium atoms; In the compound of formula II, Ar is selected from any one of single bond, C6-C40 arylene, or C6-C30 heteroarylene; In the compound of formula II, Ar1 and Ar2 are each independently selected from any one of H, C6-C40 aryl or C6-C30 heteroaryl; In the compound of formula II, A1, A2, and A3 are each independently selected from N or CR, and at least one is selected from N; R is selected from any one of H, -CN, C6-C20 aryl or C1-C12 alkyl; In the compound of formula II, a and b are each independently selected from 0 or 1, and at least one of a and b is selected from 1; In compounds of formula I and formula II, the hydrogen atoms can be independently substituted by at least one of deuterium, -F, -CN, C6-C20 aryl, triphenylmethyl, triphenylsilyl, C1-C12 alkyl or C1-C12 alkoxy.

2. The composition containing a carbazole compound according to claim 1, characterized in that, The C6-C40 arylene group is selected from any one or a combination of at least two of the following: phenylene, biphenylene, terphenylene, naphthylene, anthracene, phenanthrene, fluorene, benzo[a]fluorene, dibenzo[a]fluorene, naphthylene, pyrene, perylene, spirofluorene, phenylenetriphenylene, fluorenylene, hydrogenated benzo[a]anthrene, ind[a]fluorene, benzo[a]ind[a]fluorene, dibenzo[a]ind[a]fluorene, naphthylene, tetraphenylmethane, or benzo[a]naphthylene. Preferably, the C6-C30 heteroaryl group is selected from any one of imidazolyl, dibenzothiophene, naphthobenzofuranyl, naphthobenzothiophene, dinaphthofuranyl, dinaphthothiophene, or imidazolyl; Preferably, the C6-C40 aryl group is selected from any one or a combination of at least two of the following: phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthryl, fluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, naphthyl, pyrene, perylene, spirofluorenyl, triphenylene, fluoranyl, hydrogenated benzo[a]anthryl, ind[a]fluorenyl, benzo[a]ind[a]fluorenyl, dibenzo[a]ind[a]fluorenyl, naphthyl, tetraphenylmethane, or benzo[a]naphthyl. Preferably, the C6-C30 heteroaryl group is selected from any one or a combination of at least two of carbazolyl, dibenzothiophenel, dibenzofuranyl, naphthobenzofuranyl, naphthobenzothiophenel, dinaphthofuranyl, and dinaphthothiophenel; Preferably, the C6-C20 aryl group is selected from any one of phenyl, naphthyl, biphenyl, anthracene, phenanthryl, fluorenyl, triphenylene, or fluoranthracene. Preferably, the C1-C12 alkyl group is selected from any one of methyl, ethyl, propyl, n-butyl, tert-butyl, cyclopentyl, cyclohexyl, octyl, and adamantyl. Preferably, the C1-C12 alkoxy group is selected from any one of methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, and octoxy.

3. The composition containing a carbazole compound according to claim 1 or 2, characterized in that, In the compounds of Formula I and Formula II, Ar is independently selected from any one of single bond, phenylene, carbazolyl, biphenylene, fluorene, naphthylene, triphenylene, fluorenylene, indofluorene, dibenzothiophene, naphthanobenzofuranyl, naphthanobenzothiophene, or carbazolyl. Preferably, in the compounds of Formula I and Formula II, Ar is independently selected from at least one of single bond, phenylene, carbazolyl, naphthylene, 9,9-dimethylfluorenyl, dibenzothiophene, dibenzofuranyl or biphenylene, and more preferably any one of single bond, phenylene, biphenylene or carbazolyl; Preferably, in the compounds of Formula I and Formula II, Ar1 and Ar2 are each independently selected from any one or a combination of at least two of H, phenyl, carbazolyl, biphenyl, 9,9-dimethylfluorenyl, naphthyl, triphenylene, fluoranyl, indolefluorenyl, dibenzofuranyl, dibenzothiophene, naphthobenzofuranyl or naphthobenzothiophene. Preferably, in the compounds of Formula I and Formula II, Ar1 and Ar2 are each independently selected from at least one of H, phenyl, carbazolyl, naphthyl, 9,9-dimethylfluorenyl, dibenzothiophene, biphenyl, dibenzofuranyl, triphenylene, or fluoranyl, and more preferably at least one of phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophene, or carbazolyl; Preferably, any one of A1, A2, and A3 is selected from N, the other two are CR, and R is selected from H or -CN; Preferably, any two of A1, A2, and A3 are selected from N, the other is CR, and R is selected from H or -CN; Preferably, A1, A2, and A3 are all selected from N.

4. The composition containing a carbazole compound according to any one of claims 1-3, characterized in that, In Formula I, R1, R2, and R3 are all selected from deuterium atoms; Preferably, in Formula II, R4, R5, R6, R7, and R8 are all selected from deuterium atoms; Preferably, the hydrogen atoms in the compounds of Formula I and Formula II can each be independently substituted by at least one of -D, -F, -CN, phenyl, naphthyl, biphenyl, triphenylmethyl, triphenylsilyl, methyl, ethyl, propyl, butyl, methoxy, ethoxy, propoxy, or butoxy. Preferably, the hydrogen atoms in the compounds of Formula I and Formula II can each be independently substituted by at least one of -D, -F, -CN, phenyl, naphthyl, methyl, ethyl, tert-butylmethoxy, ethoxy, and propoxy.

5. The composition containing a carbazole compound according to any one of claims 1-4, characterized in that, The carbazole compounds are selected from any one of the following substituted or unsubstituted compounds: The substitution refers to the independent replacement of each hydrogen atom in the aforementioned carbazole compounds by a deuterium atom.

6. The composition containing a carbazole compound according to any one of claims 1-5, characterized in that, The second component includes compound A; Compound A is obtained by fusion of a group with the structure shown in Formula IA and any two adjacent carbon atoms on ring A in the group with the structure shown in Formula IB: Where * represents a fusion site; X is selected from O, S, R 301 R 302 Each is independently selected from C1-C6 alkyl, C6-C30 aryl, or C6-C20 heteroaryl, and R 301 R 302 A ring can be formed by connecting with a single key, R 303 Selected from C6-C30 aryl or C6-C20 heteroaryl, with dashed lines indicating connection sites; Ar 22 Selected from C6-C30 aryl or C6-C20 heteroaryl; In compound A, each hydrogen atom can be independently substituted by at least one of -F, -D, -CN, C6-C20 aryl, C1-C6 alkyl, and C1-C6 alkoxy, and at least one hydrogen atom in compound A is substituted by -D.

7. The composition containing a carbazole compound according to claim 6, characterized in that, In compound A, the R 303 Ar 22 Each group is independently selected from any one or a combination of two of the following substituted or unsubstituted groups: phenyl, biphenyl, naphthyl, anthracene, phenanthrene, fluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, triphenylene, fluoranyl, pyrene, perylene, spirofluorenyl, dibenzofuranyl, dibenzothiophene, naphthobenzofuran, naphthobenzothiophene, dinaphthofuran, dinaphthothiophene, hydrogenated benzene Anthrayl, indo-carbazolyl, indo-carbazolyl, terphenyl, tetraphenyl, imidazolyl, benzimidazolyl, pyridyl, pyrimidinyl, piperazine, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzoquinoxalinyl, benzoquinoxalinyl, N-phenanthroline, diazanthroline, carbazolyl, benzo-carbazolyl, naphtho-carbazolyl, dibenzo-carbazolyl, triazine; Each of the substituents is independently selected from at least one of C1-C12 alkyl, C1-C12 alkoxy, and C6-C12 aryl groups; Preferably, the R 303 Ar 22 Each group is independently selected from any one or a combination of two of the following substituted or unsubstituted groups: phenyl, biphenyl, naphthyl, phenanthryl, anthracene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl, dibenzofuranyl, dibenzothiopheneyl, triphenylene, fluorenyl, carbazoleyl, benzofluorenyl; The substituent is selected from at least one of methyl, ethyl, tert-butyl, adamantyl, cyclohexyl, cyclopentyl, 1-methylcyclopentyl, 1-methylcyclohexyl, methoxy, phenyl, biphenyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiopheneyl or naphthyl; Preferably, X is selected from O and S; Preferably, the R 301 R 302 Each is independently selected from methyl or phenyl; Preferably, the R 303 Selected from phenyl, diphenyl, or triphenyl; Preferably, the Ar 22 Selected from diphenyl, triphenyl, or tetraphenyl; Preferably, the R 303 The Ar is phenyl. 22 Selected from diphenyl, triphenyl, or tetraphenyl; Preferably, the R 303 It is a diphenyl group, and the Ar is... 22 Selected from diphenyl or triphenyl.

8. The composition containing a carbazole compound according to claim 6 or 7, characterized in that, In compound A, at least one hydrogen atom on ring A, ring B, or ring C is substituted with -D; Preferably, Ar in compound A 22 R 301 R 302 Or R 303 At least one hydrogen atom on a substituent is replaced by -D; Preferably, compound A has the structure shown in formulas I-1 to I-30, and each of the compounds shown in formulas I-1 to I-30 can be independently substituted by at least one of -F, -D, -CN, C6-C20 aryl, C1-C6 alkyl, and C1-C6 alkoxy. Among them, R 303 Ar 22 It has the same definition as claim 6.

9. The composition containing a carbazole compound according to any one of claims 6-8, characterized in that, Compound A is selected from any of the following compounds, and at least one hydrogen atom in the following compounds is substituted with -D: Preferably, compound A is selected from any one of the following compounds, and at least one hydrogen atom in the following compounds is substituted with -D: Preferably, compound A is selected from any one of the following compounds:

10. A compound, characterized in that, The compounds include compound H-601DE, compound H-601D, compound H-602DE, and compound H-603DE:

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