Composition containing carbazole compound and organic electroluminescent device

Abstract

The invention provides a composition containing a carbazole compound and an organic electroluminescent device. The composition containing the carbazole compound comprises a first component and a second component, the first component comprises a carbazole compound; the second component comprises a compound A; the carbazole compound has a structure as shown in a formula I, and the compound A is obtained by condensing any two adjacent carbon atoms on the ring A in a group with a structure as shown in a formula I-A and a group with a structure as shown in a formula I-B. According to the present invention, the structure of the carbazole compound is designed, and then the carbazole compound and the compound A are combined to obtain the composition, and the composition is suitable for being used as the main body material of the phosphorescent light emitting layer of the organic electroluminescent device so as to provide the low driving voltage, the high current efficiency and the long service life of the organic electroluminescent device.

Description

Technical Field

[0001] The invention belongs to the technical field of organic electroluminescent materials, and in particular relates to a composition containing carbazole compounds and an organic electroluminescent device. Background Art

[0002] The structure of an organic electroluminescent device is specifically: an anode, a cathode, and an organic layer therebetween. In order to improve the efficiency and stability of an organic electroluminescent element, the organic material layer includes multiple layers with different materials, such as a hole injection layer (HIL), a hole transport layer (HTL), a hole blocking layer, a light emitting layer, an electron transport layer (ETL), and an electron injection layer (EIL).

[0003] Currently, organic electroluminescence has become the mainstream display technology, and accordingly, various new OLED materials have also been developed. In order to meet people's higher requirements for OLED devices, the field urgently needs to develop more types of materials to improve the performance of OLED devices in terms of current efficiency, life span, etc. Summary of the invention

[0004] In view of the shortcomings of the prior art, the purpose of the present invention is to provide a composition containing a carbazole compound and an organic electroluminescent device, so that the composition containing the carbazole compound is suitable for being used as a main material of the phosphorescent light-emitting layer of the organic electroluminescent device, so that the organic electroluminescent device has a lower driving voltage, a higher current efficiency and a longer life.

[0005] In a first aspect, the present invention provides a composition containing a carbazole compound, wherein the composition containing a carbazole compound comprises a first component and a second component;

[0006] The first component includes a carbazole compound, and the carbazole compound has a structure shown in the following formula I:

[0007]

[0008] Among them, Ar 1 ,Ar 2 are each independently selected from any one of H, C6-C40 aryl or C6-C30 heteroaryl, and Ar 1 ,Ar 2 At least one of them is not selected from H; Ar 1 ,Ar 2 When each is independently selected from C6-C40 aryl or C6-C30 heteroaryl, Ar 1 ,Ar 2 Each independently can be connected to the adjacent benzene ring through a single bond, -O-, -S-, -NR 1 - connected into a ring;

[0009] Ar 3 ,Ar 4 Each is independently selected from any one of C6-C40 aryl or C6-C30 heteroaryl;

[0010] A 1 , A 2 , A 3 Each is independently selected from N or CR, and at least one is selected from N;

[0011] The hydrogen atoms in the compound of formula I may each independently be substituted by at least one of -D (deuterium atom), -F, -CN, C6-C20 aryl, triphenylmethyl, triphenylsilyl, C1-C12 alkyl or C1-C12 alkoxy;

[0012] The second component includes compound A, which is obtained by fusing a group with a structure as shown in formula IA with any two adjacent carbon atoms on ring A in a group with a structure as shown in formula IB:

[0013]

[0014] Among them, * indicates the fusion site;

[0015] X is selected from O, S, R 301 , R 302 are each independently selected from C1-C6 alkyl, C6-C30 aryl or C6-C20 heteroaryl, and R 301 , R 302 Can be connected to form a ring through a single bond, R 303 is selected from C6-C30 aryl or C6-C20 heteroaryl, the dotted line indicates the connection site, Ar 22 One selected from carbazolyl and dibenzofuranyl;

[0016] The hydrogen atoms in compound A may be independently substituted by at least one of -F, -D, -CN, C6-C20 aryl, C1-C6 alkyl, and C1-C6 alkoxy.

[0017] As the main material of the light-emitting layer of an organic electroluminescent device, it will be in an excited state. Therefore, the stability of the main material of the light-emitting layer in both the excited state and the ground state is important. 1 , A 2 , A 3 The situation when all are selected from N is as follows:

[0018] The Ar on the triazine ring of the compound of formula I of the present invention 1 and Ar 2 If not H, Ar on the triazine ring 1 and Ar 2Different from H and Ar on the triazine ring 1 and Ar 2 At the same time, compared with H, the electron deficiency on the triazine ring is reduced, so the composition containing the compound of formula I of the present invention is used as the main material of the light-emitting layer of the organic electroluminescent device, and its ground state stability is higher. In addition, the LUMO of the compound of formula I is mainly distributed on the triazine ring. In the excited state, Ar on the triazine ring 1 and Ar 2 When they are not H at the same time, the electrons on the triazine ring can be better dispersed, so the composition containing the compound of formula I is used as the main material of the light-emitting layer of the organic electroluminescent device, which improves the stability of the excited state of the main material of the light-emitting layer. Therefore, the use of the composition containing the compound of formula I as the main material of the light-emitting layer to prepare the organic electroluminescent device reduces the driving voltage of the organic electroluminescent device and increases the life of the organic electroluminescent device.

[0019] At the same time, the composition of the present invention containing the compound of formula I, wherein the triazine ring and the carbazole ring are substituted at the ortho position on the benzene ring, the triazine ring and the carbazole ring are in an approximately parallel position, and the composition containing the compound of formula I is used as a main material of the light-emitting layer, thereby improving the charge transport performance of the main material of the light-emitting layer, thereby improving the efficiency of the organic electroluminescent device.

[0020] In the present invention, the C6-C40 may be C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36 or C40, etc.

[0021] The C6-C30 can be C6, C8, C10, C12, C16, C20, C24, C28 or C30, etc.

[0022] It should be noted that, in the present invention, "D" represents a deuterium atom, and the same applies hereinafter.

[0023] The following are preferred technical solutions of the present invention, but are not intended to limit the technical solutions provided by the present invention. Through the following preferred technical solutions, the objectives and beneficial effects of the present invention can be better achieved and realized.

[0024] As a preferred technical solution of the present invention, the C6-C40 aromatic group is selected from any one or a combination of at least two of phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, fluorenyl, benzofluorenyl, dibenzofluorenyl, naphthfluoroenyl, pyrene, peryl, spirofluorenyl, triphenylene, fluoranthenyl, hydrogenated benzanthryl, indenofluorenyl, benzoindenofluorenyl, dibenzoindenofluorenyl, naphthfluoroenyl, tetraphenylmethane or benzonaphthofluorenyl.

[0025] As a preferred technical solution of the present invention, the C6-C30 heteroaryl group is selected from any one of carbazolyl, dibenzothiophenyl, dibenzofuranyl, naphthiobenzofuranyl, naphthiobenzothiophenyl, dinaphthofuranyl, and dinaphthothiophenyl, or a combination of at least two thereof.

[0026] Preferably, the C6-C20 aryl group is selected from any one of phenyl, naphthyl, biphenyl, anthracenyl, phenanthryl, fluorenyl, triphenylene or fluoranthene.

[0027] Preferably, the C1-C12 alkyl group is selected from any one of a methyl group, an ethyl group, a propyl group, a n-butyl group, a tert-butyl group, a cyclopentyl group, a cyclohexyl group, an octyl group and an adamantyl group.

[0028] Preferably, the C1-C12 alkoxy group is selected from any one of methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy and octyloxy.

[0029] As a preferred technical solution of the present invention, the Ar 1 ,Ar 2 Each is independently selected from at least one of H, phenyl, carbazolyl, naphthyl, 9,9-dimethylfluorenyl, dibenzothiophenyl, biphenyl, dibenzofuranyl, triphenylene or fluoranthenyl, more preferably phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, 9,9-dimethylfluorenyl, carbazolyl;

[0030] The Ar 1 ,Ar 2 At least one of them is not selected from H; and the Ar 1 ,Ar 2 When not selected from H, Ar 1 ,Ar 2 Each independently can be connected to the adjacent benzene ring through a single bond, -O-, -S-, -NR 1 - connected into a ring;

[0031] The R 1 Has the same definition as above.

[0032] Preferably, the Ar 1 Any one selected from phenyl, naphthyl or biphenyl, wherein Ar 1 Select from the group consisting of -O-, -S-, -NR 1 - connected into a ring;

[0033] The R 1 Selected from phenyl or naphthyl.

[0034] Preferably, the Ar 2 As a preferred technical solution of the present invention, Ar3 ,Ar 4 Each is independently selected from at least one of phenyl, carbazolyl, naphthyl, 9,9-dimethylfluorenyl, dibenzothiophenyl, biphenyl, dibenzofuranyl, triphenylene or fluoranthenyl, and more preferably at least one of phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, 9,9-dimethylfluorenyl and carbazolyl.

[0035] Preferably, the Ar 3 ,Ar 4 Each is independently selected from any one of phenyl, naphthyl or biphenyl.

[0036] As the preferred technical solution of the present invention, A 1 , A 2 , A 3 One of them is selected from N, the other two are selected from CR, and the R is selected from H.

[0037] As the preferred technical solution of the present invention, A 1 , A 2 , A 3 Two of them are selected from N, another one is selected from CR, and the R is selected from H.

[0038] As the preferred technical solution of the present invention, A 1 , A 2 , A 3 All are selected from N.

[0039] As a preferred technical solution of the present invention, the hydrogen atoms in the compound of formula I can be independently replaced by at least one of -D, -F, -CN, phenyl, naphthyl, biphenyl, triphenylmethyl, triphenylsilyl, methyl, ethyl, propyl, butyl, methoxy, ethoxy, propoxy or butoxy.

[0040] Preferably, the hydrogen atoms in the compound of formula I can be independently substituted by at least one of -D, -F, -CN, phenyl, naphthyl, methyl, ethyl, tert-butyl, methoxy, ethoxy and propoxy.

[0041] As a preferred technical solution of the present invention, the carbazole compound is selected from any one of the following substituted or unsubstituted compounds:

[0042]

[0043]

[0044]

[0045] The substitution means that each of the hydrogen atoms in the above-mentioned carbazole compounds can be independently substituted by a deuterium atom. Preferably, the carbazole compound is selected from any one of the following compounds:

[0046]

[0047]

[0048] In the compound A of the present invention, the C6-C30 can be C6, C10, C12, C18, C24 or C30, etc.

[0049] The C6-C20 can be C6, C10, C12, C18 or C20, etc.

[0050] The C1-C6 can be C1, C2, C3, C4, C5 or C6.

[0051] As a preferred technical solution of the present invention, the R 303 is selected from any one or a combination of at least two of the following substituted or unsubstituted groups: phenyl, biphenyl, naphthyl, anthracenyl, phenanthryl, fluorenyl, benzofluorenyl, dibenzofluorenyl, triphenylene, fluoranthenyl, pyrenyl, perylenyl, spirofluorene, dibenzofuranyl, dibenzothiophenyl, naphthobenzofuran, naphthobenzothiophene, dinaphthofuran, dinaphthothiophene, hydrogenated benzanthracenyl, indeno[1,2-b]fluorene, indolocarbazole, indolocarbazole, terphenyl, quaterphenyl, imidazolyl, benzimidazolyl, pyridyl, pyrimidinyl, piperazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzoquinoxalinyl, benzoquinazolinyl, N-phenanthryl, diazaphenanthryl, carbazolyl, benzocarbazolyl, naphthocarbazolyl, dibenzocarbazolyl, triazinyl;

[0052] The substituents of the substitution are independently selected from at least one of C1-C12 (such as C1, C2, C5, C6, C8, C10 or C12, etc.) alkyl, C1-C12 (such as C1, C2, C5, C6, C8, C10 or C12, etc.) alkoxy, and C6-C12 (such as C6, C7, C8, C9, C10, C11 or C12) aryl.

[0053] As a preferred technical solution of the present invention, the R 303 are independently selected from any one or a combination of at least two of the following substituted or unsubstituted groups: phenyl, biphenyl, naphthyl, phenanthryl, anthracenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorene, dibenzofuranyl, dibenzothiophenyl, triphenylene, fluorenyl, benzofluorenyl, carbazolyl;

[0054] The substituted 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, dibenzothiophenyl or naphthyl.

[0055] Preferably, X is selected from O and S.

[0056] Preferably, the R 301 , R 302 Each is independently selected from methyl or phenyl.

[0057] Preferably, the R 303 Any one selected from phenyl, diphenyl or terphenyl.

[0058] Preferably, the R 303 It is phenyl.

[0059] Preferably, the R 303 It is a diphenyl group.

[0060] As a preferred technical solution of the present invention, the compound A has a structure as shown in formulas I-1 to I-30: and the compounds shown in formulas I-1 to I-30 can each independently be substituted by at least one of -F, -CN, C6-C20 (for example, C6, C10, C12, C18 or C20, etc.) aryl, C1-C6 (for example, C1, C2, C3, C4, C5 or C6) alkyl, and C1-C6 (for example, C1, C2, C3, C4, C5 or C6) alkoxy;

[0061]

[0062] Among them, R 303 ,Ar 22 Has the same protection scope as above.

[0063] As a preferred technical solution of the present invention, the compound A is selected from any one of the following compounds:

[0064]

[0065] Preferably, the compound A is selected from any one of the following compounds:

[0066]

[0067] It should be noted that there is no special limitation on the preparation method of the above-mentioned compound A in the present invention, and any commonly used preparation methods in the art are applicable.

[0068] In a second aspect, 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;

[0069] The organic thin film layer material includes the composition containing carbazole compounds as described in the first aspect.

[0070] As a preferred technical solution 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 containing carbazole compounds as described in the first aspect.

[0071] Preferably, the light-emitting layer is a phosphorescent light-emitting layer. The main material of the phosphorescent light-emitting layer includes the composition containing carbazole compounds as described in the first aspect.

[0072] As a preferred technical solution of the present invention, the organic electroluminescent device is a green organic electroluminescent device.

[0073] The luminescent layer in the present invention includes a luminescent layer main material and a doping material, wherein the doping material is also called a dye or a phosphorescent luminescent material. The luminescent layer main material can be a single compound or a mixture of two or more compounds.

[0074] The light-emitting layer includes a phosphorescent light-emitting layer, and the phosphorescent light-emitting layer 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.

[0075] The volume percentage of the main material in the phosphorescent layer is 60% to 99.9% (for example, it can be 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, 98% or 99.9%, etc.), preferably 70% to 99.5%, and more preferably 85% to 95%.

[0076] In the present invention, the doping material of the light-emitting layer may be a phosphorescent material, which is also called a triplet light-emitting material, and refers to the light emitted from a substance in a triplet excited state. The specific selection of the phosphorescent material in the present invention is not particularly limited, and the doping materials of the light-emitting layer commonly used in the art are applicable, including but not limited to: a compound having a structure shown in the following formula PD:

[0077]

[0078] Wherein, M is selected from any one of Ir, Pt, Pd, Os, Ti, Zr, Hf, Eu, Tb, Tm, Cu or Au;

[0079] Y 1 -Y 4 are each independently selected from carbon or nitrogen;

[0080] Y 1 and Y 2 They can be connected by single or double bonds. 3 and Y 4 They can be connected by single or double bonds;

[0081] Cy 1 and Cy 2 Each is independently selected from phenyl, naphthyl, fluorenyl, spirofluorenyl, indenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, benzimidazolyl, benzofuranyl, benzothienyl, isobenzothienyl, benzimidazolyl, benzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzothienyl, N-heterocarbazolyl, wherein Cy 1 and Cy 2 may optionally be linked to each other via a single bond or an organic linking group;

[0082] Any two ligands of M, or more than two ligands, may be connected by a single bond or a double bond, or may be bridged by O or S, or may be connected by any chemical group or chemical structure to form a structural form that conforms to chemical principles;

[0083] R 91 and R 92 Each is independently selected from -H, -D, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid, carboxylate, sulfonic acid, sulfonate, phosphoric acid, phosphate, -SF 5, substituted or unsubstituted C1-C60 (for example, C1, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55 or C60, etc.) alkyl, substituted or unsubstituted C2-C60 (for example, C2, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55 or C60, etc.) alkenyl, substituted or unsubstituted C2-C60 (e.g., C2, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55, or C60, etc.) alkynyl, substituted or unsubstituted C1-C60 (e.g., C1, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55, or C60, etc.) alkoxy, substituted or unsubstituted C2-C10 (for example, C2, C3, C4, C5, C6, C7, C8, C9 or C10) heterocycloalkyl, substituted or unsubstituted C6-C60 (for example, C6, C12, C15, C18, C24, C30, C32, C36, C40, C42, C54 or C60, etc.) aryl, substituted or unsubstituted C6-C60 (for example, C6, C12, C15, C18, C24, C30, C32, C36, C40, C42, C54 or C60, etc.) any one of a C24, C30, C32, C36, C40, C42, C54 or C60 (e.g., C24, C30, C32, C36, C40, C42, C54 or C60, etc.) aryloxy group, a substituted or unsubstituted C6-C60 (e.g., C6, C12, C15, C18, C24, C30, C32, C36, C40, C42, C54 or C60, etc.) arylthio group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, and a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group.

[0084] a 1 and a 2 Each is independently an integer selected from 1-5, for example, 1, 2, 3, 4 or 5;

[0085] b is an integer selected from 0-4, for example, 0, 1, 2, 3 or 4;

[0086] a is selected from 1, 2 or 3;

[0087] L 1 It is a monovalent organic ligand, a divalent organic ligand or a trivalent organic ligand.

[0088] Preferably, the compound of formula PD is selected from any one of the following compounds:

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095] In the present invention, the organic thin film layer includes a hole layer, and the hole layer includes a hole injection layer, a hole transport layer and an electron blocking layer.

[0096] The hole injection layer material includes a P-type dopant. The P-type dopant refers to a dopant that coexists with the hole injection layer material in the OLED device and can oxidize the hole injection layer material, thereby acting as an electron acceptor and promoting the movement of holes in the hole injection layer to the anode. In the present 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.

[0097] The P-type dopant is present in the hole injection layer in a volume percentage of 1% to 10% (eg, 1%, 2%, 4%, 6%, 8% or 10%).

[0098] In the present invention, there is no particular limitation on the type of P-type dopant. For example, the compounds D-1 to D-13 disclosed in CN113728453A or the compounds HI-1 to HI-9 described below can be selected:

[0099]

[0100]

[0101] In the present invention, the hole layer material (including the hole injection layer, the hole transport layer and the electron blocking layer) has a structure shown in the following formula HT-GH4:

[0102]

[0103] Among them, L 41 is selected from a single bond, a C6-C40 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36, or C40, etc.) aryl, or a C6-C20 (e.g., C6, C8, C10, C12, C16, or C20, etc.) heteroaryl;

[0104] Ar 41 ,Ar 42Each is independently selected from C6-C40 (for example, C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36 or C40, etc.) aryl, C6-C20 (for example, C6, C8, C10, C12, C16 or C20, etc.) heteroaryl;

[0105] X is selected from CR 41 R 42 or NR 43 , where R 41 , R 42 , R 43 are each independently selected from substituted or unsubstituted phenyl (the substituted substituent is selected from C1-C6 (for example, C1, C2, C3, C4, C5 or C6) alkyl, C1-C6 (for example, C1, C2, C3, C4, C5 or C6) alkoxy, naphthyl, triphenylene, fluoranthene, 9,9-dimethylfluorenyl, biphenyl, substituted or unsubstituted group (the substituted substituent is phenyl), substituted or unsubstituted dibenzothienyl (the substituted substituent is phenyl), substituted thienyl, C1-C6 (for example, C1, C2, C3, C4, C5 or C6) alkyl, any one of R 41 , R 42 They can be linked to form rings via single bonds.

[0106] The compound of formula HT-GH4 is selected from any one of the following compounds:

[0107]

[0108]

[0109]

[0110] In the present invention, the hole layer material (including the hole injection layer, the hole transport layer and the electron blocking layer) also includes a compound having a structure shown in the following formula IA or a compound having a structure shown in the following formula IB:

[0111]

[0112] Wherein, L is selected from any one of C6-C40 (for example, C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36 or C40, etc.) arylene, dibenzofuranyl or dibenzothiophenyl;

[0113] 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;

[0114] Ar is selected from any one of triphenylene, fluoranthenylene, dibenzofuranylene or dibenzothiophenylene;

[0115] Ar 1 and Ar 2 Each is independently selected from any one of a C6-C40 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36 or C40, etc.) aryl group, dibenzofuran or dibenzothiophenyl group;

[0116] Ar 1 Between Ar and Ar 2 and Ar 1 ,Ar 2 Each of them can be independently connected by a single bond, O, S, CR 1 R 2 , NR connection or bridging.

[0117] R, R 1 , R 2 Each is independently selected from any one of C1-C20 (for example, C1, C2, C4, C6, C8, C10, C12, C14, C16, C18 or C20, etc.) alkyl, C6-C40 (for example, C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36 or C40, etc.) aryl, dibenzofuranyl or dibenzothiophenyl;

[0118] H in the compound of formula IB and the compound of formula IA can each independently be replaced by at least one of -F, -CN, -D (deuterium atom), C1-C6 alkyl, C1-C6 alkoxy, phenyl, biphenyl, naphthyl, phenanthryl, anthracenyl, fluorenyl, benzofluorenyl, dibenzofluorenyl, triphenylene, fluoranthenyl, pyrenyl, perylenyl, spirofluorenyl, indenofluorenyl or hydrogenated benzanthryl.

[0119] Preferably, Ar is a fluoranthenyl group, and m+n>1.

[0120] Preferably, H in the compound of formula IB and the compound of formula IA can be replaced by at least one of -F, -CN, -D, C1-C3 alkyl (for example, methyl, ethyl or propyl), C1-C3 alkoxy (for example, methoxy, ethoxy or propoxy), phenyl, biphenyl, triphenylene, and fluoranthene.

[0121] Preferably, the L, Ar 1 ,Ar 2Each is independently selected from at least one of phenyl, biphenyl, naphthyl, phenanthryl, anthracenyl, fluorenyl, benzofluorenyl, dibenzofluorenyl, triphenylene, fluoranthenyl, pyrenyl, peryl, spirofluorenyl, indenofluorenyl and hydrogenated benzanthryl.

[0122] Preferably, the compound of formula IB is selected from any one of the following compounds 1-112:

[0123]

[0124] In the OLED device provided by the present invention, the hole layer material may include conventional hole materials in the art in addition to the compound described in formula HT-GH4, the compound of formula IB, and the compound of formula IA, without special restrictions. Exemplary includes but is not limited to: triarylamine compounds or carbazole compounds. Triarylamine compounds or carbazole compounds containing more than 3 N atoms are preferred, because the HOMO of triarylamine compounds or carbazole compounds containing more than 3 N atoms is higher (smaller absolute value), and is more suitable for use as hole injection layer materials. Triarylamine compounds or carbazole compounds containing 2 or 1 N atoms can be used as hole transport layer materials. Some compounds or carbazole compounds containing 1 N atom, if they have a higher LUMO, can also be used as electron blocking layer materials.

[0125] The triarylamine compound or the carbazole compound is used as the hole layer material, and the hole layer material includes the following structure:

[0126]

[0127] Among them, Ar 601 ~Ar 609 Each independently selected from a substituted or unsubstituted C6-C40 (for example, C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36 or C40, etc.) aryl, a substituted or unsubstituted dibenzothienyl, a substituted or unsubstituted naphthobenzofuranyl, a substituted or unsubstituted naphthobenzothienyl, a substituted or unsubstituted dinaphthofuranyl, a substituted or unsubstituted dinaphthothienyl;

[0128] And Ar 601 ~Ar 609 Ar atoms adjacent to or connected to the same N atom 601 ~Ar 609 , can be connected by single key or through O, S, CR 701 , R 702 NR 703 bridging;

[0129] R 701, R 702 , R 703 is selected from C6-C40 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36, or C40, etc.) aromatic groups, C6-C20 (e.g., C6, C8, C10, C12, C16, or C20, etc.) heteroaryl groups, C1-C6 (e.g., C1, C2, C3, C4, C5, or C6) alkyl groups, and R 701 , R 702 Can connect via one-touch.

[0130] The hole blocking layer (HBL) can confine holes and / or excitons within the EL to improve the current efficiency and lifetime of the device. Compared with the EL material closest to the HBL interface, the HBL material has a lower HOMO (larger absolute value) and / or higher triplet energy.

[0131] The electron transport layer (ETL) may include a material capable of transporting electrons. The electron transport layer may be intrinsic (undoped) or doped, and doping may be used to enhance conductivity. In the present invention, there is no particular restriction on the ETL material, and any metal complex or organic compound may be used as long as it can transport electrons. The general electron transport layer material contains the following structural fragments: at least one of a pyridine structure, a pyrimidine structure, a triazine structure, a benzimidazole structure, a benzoxazole structure, a benzothiazole structure, an N-naphthalene structure, an N-coffee structure, an N-carbazole structure, and an N-dibenzothiophene structure.

[0132] In the present invention, there is no special restriction on the electron transport layer material, which exemplarily includes but is not limited to:

[0133]

[0134] In the present invention, the material of the cathode is a metal with a low work function (e.g., alkaline earth metal, alkali metal, main group metal or lanthanide element (e.g., Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.)), a metal alloy composed of multiple metals (alloy composed of alkali metal or alkaline earth metal 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 functions, such as Ag or Al, can also be used. In this case, a combination of the metals is usually used, such as Ca / Ag, Mg / Ag or Ba / Ag.

[0135] It is also possible to introduce a thin intermediate layer of a material with a high dielectric constant between the metal cathode and the organic semiconductor to form a multi-layer structure; the material with a high dielectric constant can also be called an electron injection material, and fluorides of alkali metals or alkaline earth metals, as well as corresponding oxides or carbonates (such as LiF, Li 2 O, BaF 2 , MgO, NaF, CsF, Cs 2 CO 3 etc.) or lithium quinolate (LiQ) can be selected.

[0136] Compared with the prior art, the present invention has the following beneficial effects:

[0137] Firstly, the present invention designs the structure of the carbazole compound, and then combines the carbazole compound with Compound A to obtain a composition, which is suitable for use as the host material of the phosphorescent light-emitting layer of the organic electroluminescent device, enabling the organic electroluminescent device to have a lower driving voltage, higher current efficiency, and longer lifespan. Detailed implementation modes

[0138] To facilitate the understanding of the present invention, the following examples are listed. Those skilled in the art should understand that the examples are only for helping to understand the present invention and should not be regarded as specific limitations on the present invention.

[0139] The specific structures of some compounds used in the following examples and comparative examples of the present invention are as follows:

[0140]

[0141]

[0142] Example 1

[0143] This example provides a green organic electroluminescent device, and the composition containing the carbazole compound provided by the present invention is used as the host material of its light-emitting layer. Specifically, the light-emitting layer in this example is a phosphorescent light-emitting layer, and the host material of the light-emitting layer is a composition formed by Compound P1 and Compound HE, and the volume ratio of the two is 1:1.

[0144] The structure of the green organic electroluminescent device is: ITO / HT-1(60nm) / EB-1(20nm) / Host material of light-emitting layer: PGD-1[5%](35nm) / ETL-1(25nm) / LiF(0.5nm) / Al(150nm).

[0145] Among them, HT-1 is a hole transport material;

[0146] EB-1 is an electron blocking layer;

[0147] PGD-1[5%] refers to the doping ratio of the dye, that is, the volume ratio of the combination of the phosphorescent light-emitting layer host material compound P1 and compound HE to the dye PGD-1 is 95:5.

[0148] The preparation method of the green organic electroluminescent device is as follows:

[0149] The material was placed in a vacuum chamber and evacuated to 1×10 -5 ~1×10 -6 Pa was vacuum evaporated onto the cleaned ITO substrate in turn to prepare an OLED device.

[0150] Examples 2-6 and Comparative Examples 1-2

[0151] Examples 2-6 and Comparative Examples 1-2 respectively provide a green organic electroluminescent device, which differs from Example 1 only in that the main material of the phosphorescent light-emitting layer is replaced with other compositions, as shown in Table 1 below. The rest is the same as Example 1.

[0152] Performance Testing

[0153] The voltage, brightness, current efficiency and LT95 of the green organic electroluminescent devices provided in Examples 1-6 and Comparative Examples 1-2 were tested, wherein the voltage and current efficiency were the values ​​of the green organic electroluminescent devices with a brightness of 1000 cd / m 2 The corresponding value, LT95, refers to maintaining the initial current density of the device at 10mA / cm 2 The time required for the device efficiency to drop to 95% of the efficiency corresponding to the initial current density is constant. The driving voltage, current efficiency and LT95 are relative values. The specific test results are shown in Table 1 below.

[0154] Table 1: Composition of main materials of light-emitting layer and device performance test results of Examples 1-6 and Comparative Examples 1-2

[0155]

[0156] As can be seen from Table 1, Examples 1-6 have higher current efficiency and longer lifespan. Therefore, the present invention first designs the structure of the carbazole compound and then combines the carbazole compound with compound A to obtain a composition suitable for use as a main material for the phosphorescent light-emitting layer of an organic electroluminescent device.

[0157] In summary, in the present invention, the structure of the carbazole compound is designed, and then the carbazole compound is combined with a second component to obtain a composition, so that it is suitable for use as a main material of the phosphorescent light-emitting layer of an organic electroluminescent device, so that the organic electroluminescent device has a lower driving voltage, a higher current efficiency and a longer life.

[0158] The applicant declares that the present invention illustrates the detailed process flow of the present invention through the above-mentioned embodiments, but the present invention is not limited to the above-mentioned detailed process flow, that is, it does not mean that the present invention must rely on the above-mentioned detailed process flow to be implemented. Those skilled in the art should understand that any improvement of the present invention, equivalent replacement of various raw materials of the product of the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. A composition containing a carbazole compound, characterized in that: comprising a first component and a second component; The first component is selected from at least one of the compounds shown in the following formula I: In Formula I, Ar1 and Ar2 are each independently selected from any one of H, C6-C40 aryl, and C6-C30 heteroaryl, and at least one of Ar1 and Ar2 is not H; if Ar1 and Ar2 are not H, Ar1 and Ar2 can each independently be connected to the adjacent benzene ring through any one of a single bond, -O-, -S-, and -NR1- to form a ring, wherein R1 is selected from any one of C6-C20 aryl and C1-C12 alkyl; Ar3 and Ar4 are each independently selected from any one of C6-C40 aryl and C6-C30 heteroaryl; A1, A2, A3 are each independently selected from N or CR, and at least one of A1, A2, A3 is N; R is selected from any one of H, -CN, C6-C20 aryl, and C1-C12 alkyl; The hydrogen atoms in the compound represented by formula I can be independently substituted by any one of -D (deuterium atom), -F, -CN, C6-C20 aryl, triphenylmethyl, triphenylsilyl, C1-C12 alkyl or C1-C12 alkoxy; The second component includes compound A; The compound A is obtained by fusing the group of the structure shown in formula IA with any two adjacent carbon atoms on the ring A in the group of the structure shown in formula IB: Among them, * indicates the fusion site; X is selected from O, S, or R 301 , R 302 are each independently selected from C1-C6 alkyl, C6-C30 aryl or C6-C20 heteroaryl, and R 301 , R 302 Can be connected to form a ring through a single bond; R 303 is selected from C6-C30 aryl or C6-C20 heteroaryl; the dotted line indicates the attachment site; Ar 22 One selected from carbazolyl and dibenzofuranyl.

2. The composition according to claim 1, characterized in that In Formula I, the C6-C30 heteroaryl group is selected from any one of carbazolyl, dibenzothiophenyl, dibenzofuranyl, naphthobenzofuranyl, naphthobenzothiophenyl, dinaphthofuranyl and dinaphthothiophenyl; The C6-C20 aryl group is selected from any one of phenyl, naphthyl, biphenyl, anthracenyl, phenanthryl, fluorenyl, triphenylene or fluoranthenyl; The C1-C12 alkyl group is selected from any one of methyl, ethyl, propyl, n-butyl, tert-butyl, cyclopentyl, cyclohexyl, octyl and adamantyl; The C1-C12 alkoxy group is selected from any one of methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy and octyloxy.

3. The composition according to claim 1, characterized in that In Formula I, Ar1 and Ar2 are each independently selected from at least one of H, phenyl, carbazolyl, naphthyl, 9,9-dimethylfluorenyl, dibenzothiophenyl, biphenyl, dibenzofuranyl, triphenylene or fluoranthene, preferably any one of phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, 9,9-dimethylfluorenyl and carbazolyl, and at least one of Ar1 and Ar2 is not H; if Ar1 and Ar2 are not H, Ar1 and Ar2 can each independently be connected to the adjacent benzene ring through a single bond, -O-, -S-, or -NR1- to form a ring; Ar3 and Ar4 are each independently selected from at least one of phenyl, carbazolyl, naphthyl, 9,9-dimethylfluorenyl, dibenzothiophenyl, biphenyl, dibenzofuranyl, triphenylene or fluoranthene, preferably any one of phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, 9,9-dimethylfluorenyl and carbazolyl.

4. The composition according to claim 1, characterized in that In Formula I, one of A1, A2, and A3 is N, and the other two are CR, wherein R is H; or two of A1, A2, and A3 are N, and the other one is CR, wherein R is H; or A1, A2, and A3 are all N; Preferably, the hydrogen atoms in the compound of formula I can 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 compound of formula I can be independently substituted by at least one of -D, -F, -CN, phenyl, naphthyl, methyl, ethyl, tert-butyl, methoxy, ethoxy and propoxy.

5. The composition according to claim 1, characterized in that The compound of formula I is selected from any one of the following substituted or unsubstituted compounds: The substitution means that the hydrogen atoms in the above carbazole compounds can be independently replaced by deuterium atoms; preferably, the carbazole compounds are selected from any one of the following compounds:

6. The composition according to claim 1, characterized in that In compound A, R 303 Any one or a combination of at least two selected from the following substituted or unsubstituted groups: phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, benzofluorenyl, dibenzofluorenyl, triphenylene, fluoranthenyl, pyrenyl, peryl, spirofluorenyl, dibenzofuranyl, dibenzothiophenyl, naphthobenzofuran, naphthobenzothiophene, dinaphthofuran, dinaphthothiophene, hydrogenated benzanthryl, indenofluorenyl, indolecarbazolyl, indenocarbazolyl, terphenyl, Quadruphenyl, imidazolyl, benzimidazolyl, pyridyl, pyrimidyl, piperazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, benzoquinoxalinyl, benzoquinazolinyl, N heterophenanthrenyl, diazophenanthrenyl, carbazolyl, benzocarbazolyl, naphthocarbazolyl, dibenzocarbazolyl, triazinyl; the substituted substituents are each independently selected from at least one of C1-C12 alkyl, C1-C12 alkoxy, and C6-C12 aryl; Preferably, the R 303 Each is independently selected from any one or a combination of at least two of the following substituted or unsubstituted groups: phenyl, biphenyl, naphthyl, phenanthryl, anthracenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl, dibenzofuranyl, dibenzothienyl, triphenylene, fluorenyl, benzofluorenyl, carbazolyl; the substituted 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, dibenzothienyl or naphthyl.

7. The composition according to claim 1, characterized in that In compound A, X is selected from O and S; Preferably, the R 301 , R 302 Each independently selected from methyl or phenyl; Preferably, the R 303 Any one selected from phenyl, diphenyl or terphenyl; Preferably, the R 303 is phenyl; Preferably, the R 303 It is a diphenyl group.

8. The composition according to claim 1, characterized in that Compound A has a structure as shown in formula I-1 to I-30: and the compounds shown in formula I-1 to I-30 can each independently be substituted by at least one of -F, -CN, C6-C20 aryl, C1-C6 alkyl, and C1-C6 alkoxy; Preferably, the compound A is selected from any one of the following compounds: Preferably, the compound A is selected from any one of the following compounds:

9. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises an anode, a cathode and an organic thin film layer arranged between the anode and the cathode, and the material of the organic thin film layer comprises the composition according to any one of claims 1 to 8.

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