Light-emitting material composition and organic electroluminescent device comprising the same

Abstract

This invention provides a luminescent material composition and an organic electroluminescent device comprising the luminescent material composition. The luminescent material composition provided by this invention includes a first host material and a second host material, wherein the first host material has a structure represented by formula H-L-E, wherein H has the structure shown in formula (I), E has the structure shown in formula (II), and L is selected from the group consisting of arylene groups having 6-30 carbon atoms or heteroarylene groups having 3-30 carbon atoms; the second luminescent material has a structure as shown in formula (III). Organic electroluminescent devices prepared using this luminescent material composition as the host material of the luminescent layer exhibit higher luminous efficiency and / or longer lifetime characteristics.

Description

Technical Field

[0001] This invention relates to the field of luminescent materials, and in particular, to a luminescent material composition and its application in organic electroluminescent devices. Background Technology

[0002] In 1987, Tang et al. from Eastman Kodak first reported a green electroluminescent device made of a double-layer organic thin film. The device used indium tin oxide (ITO) as the anode, on which a 75 nm thick amorphous, pinhole-free aromatic diamine film was deposited for hole transport. Then, a 60 nm thick 8-hydroxyquinoline aluminum film was deposited on the aromatic diamine film as both an electron transport layer and a light-emitting layer. A magnesium-silver alloy was used as the cathode. This double-layer film structure successfully reduced the turn-on voltage to 5.5 V and achieved high emissivity (>1000 cd·m⁻¹). -2 With a wavelength of 550 nm and an external quantum efficiency of 1.0%, it has great practical significance. In 1994, KH1do et al. from Japan first fabricated an organic electroluminescent device that emits white light. They doped three fluorescent dyes of blue, green, and orange into a poly(N-vinylcarbazole) (PVK) film as a hole transport layer and emission layer, used a 1,2,4-triazole derivative (TAZ) as a hole blocking layer, and 8-hydroxyquinoline aluminum (Alq3) as an electron transport layer. The device was composed of a multilayer structure of glass substrate / ITO / PVK / TAZ / Alq3 / Mg:Ag. Under a driving voltage of 14V, they achieved a wide coverage of the visible light region and a brightness of up to 3400 cd·m. -2 The high-brightness white light emission is achieved by doping a polymer film with fluorescent compounds of multiple colors to form a single light-emitting layer. This discovery by KIdo et al. has significantly advanced the application of organic electroluminescence, opening the door to the use of organic light-emitting devices in lighting and promoting their further development.

[0003] Organic light-emitting devices emit light in two forms: fluorescence and phosphorescence. Fluorescence is emitted using the energy of singlet excitons, while phosphorescence is emitted using the energy of both singlet and triplet excitons. Because the ratio of singlet to triplet excitons is fixed at 1:3, theoretically, the internal quantum efficiency of fluorescent devices using only singlet excitons is at most 25%, while the internal quantum efficiency of phosphorescent devices can reach 100%.

[0004] Currently, organometallic complexes and organic electroluminescent devices with phosphorescence emission have been reported, but in many applications such as TVs and lighting equipment, the lifetime of OLEDs is insufficient, and higher efficiency OLEDs are still needed. Typically, the higher the brightness of an OLED, the shorter its lifetime. Therefore, for displays requiring long-term use and high resolution, OLEDs with high luminous efficiency or long lifetime are needed, thus necessitating the development of host materials that can improve OLED performance. Summary of the Invention

[0005] The purpose of this invention is to provide an organic electroluminescent material composition as the main material for organic electroluminescent devices, thereby preparing organic electroluminescent devices with higher luminous efficiency and / or longer lifetime characteristics.

[0006] To achieve the above objectives, a first aspect of the present invention provides a luminescent material composition comprising a first host material and a second host material, wherein the first host material has a structure represented by formula HLE, wherein H has a structure represented by formula (I):

[0007]

[0008] In formula (I), ring 1, ring 2, ring 3 and ring 4 are each independently selected from unsaturated carbon rings having 5-30 carbon atoms or unsaturated carbon heterocycles having 3-30 carbon atoms.

[0009] T is selected from O, S, Se, NR N SiR a R b PR or BR;

[0010] R X Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;

[0011] L is selected from the group consisting of arylene groups having 6-30 carbon atoms or heteroarylene groups having 3-30 carbon atoms; optionally, the arylene group or heteroarylene group involved in L is surrounded by one or more R groups. L Replaced;

[0012] E has the structure represented by equation (II):

[0013]

[0014] In equation (II), Z1 to Z5 are the same or different, and are each independently selected from NR. N or CR a R b And at least one of Z1 to Z5 is selected from NR N ;

[0015] R, R X R N R L R a and R b The same or different, each independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocycloalkyl groups having 3-20 carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted... Alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, and substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0016] Optionally, adjacent substituents R, R X R N R L R a and R b The connection forms a loop;

[0017] The asterisk (*) indicates the location where the L bond is formed.

[0018] The second main material has a structure as shown in formula (Ⅲ):

[0019]

[0020] In equation (Ⅲ), X and Y are each independently selected from -N= and -NR=. 10 -, -O-, or -S-, where Y represents -NR when X represents -N=. 11 -, -O-, or -S-, or when X represents -NR 10 When -, Y represents -N=, -O-, or -S-;

[0021] HAr is selected from substituted or unsubstituted C3-C atoms containing one or more nitrogen atoms. 30 Mixed aromatics;

[0022] L2 is selected from single-bonded, substituted, or unsubstituted C6-C bonds. 30aryl, substituted or unsubstituted C3-C 30 heteroaryl;

[0023] R1 is selected from substituted or unsubstituted C6-C. 30 aryl, substituted or unsubstituted C3-C 30 Mixed aromatics;

[0024] R2, R3, R4, R 10 and R 11 Each is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C. 30 Alkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl, substituted or unsubstituted C3-C 30 cycloalkyl, substituted or unsubstituted C1-C 30 Alkoxy, substituted or unsubstituted tri(C1-C) 30 )alkylsilyl, substituted or unsubstituted di(C1-C2) 30 )alkyl (C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 )alkyl di(C6-C 30 arylsilyl, substituted or unsubstituted tri(C6-C) 30 ) arylsilyl, substituted or unsubstituted mono- or di-(C1-C) 30 )alkylamino, substituted or unsubstituted mono- or di-(C6-C) 30 ) arylamino, substituted or unsubstituted (C1-C 30 )alkyl (C6-C 30 )Arylamino; Optionally, any two adjacent groups in R2, R3 and R4 are linked together to form a ring;

[0025] b′ and c′ are each independently selected from 1 or 2; d′ is selected from 1, 2, 3 or 4; wherein, when b′, c′ and d′ are each independently greater than 1, each of R2, R3 and R4 is the same or different.

[0026] According to some embodiments of the present invention, the alkyl group having 1-20 carbon atoms includes straight-chain alkyl groups having 1-20 carbon atoms and branched-chain alkyl groups having 3-20 carbon atoms. According to some embodiments of the present invention, the straight-chain alkyl group having 1-20 carbon atoms refers to a group with the general formula C1. n H 2n+1 - a straight-chain alkyl group, wherein n is 1-20.

[0027] According to some embodiments of the present invention, the branched alkyl group having 2-40 carbon atoms or the cycloalkyl group having 3-20 carbon atoms includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, tert-butyl, isopropyl and other groups.

[0028] According to some embodiments of the present invention, the aryl group having 6-30 carbon atoms is an aromatic hydrocarbon group, such as phenyl, biphenyl, naphthyl, anthraceneyl, phenanthryl, pyrene, etc., and the substituents of the aryl group can be alkyl, halogen, phenyl, etc.

[0029] According to some embodiments of the present invention, the heteroaryl group having 3-30 carbon atoms can be a heteroaryl group containing any one or more of the heteroatoms N, O, S, and P, for example, it can be a group containing a five-membered heterocycle, a six-membered heterocycle, a benzo[a]heterocycle, a heterocyclic fused-ring heterocycle, a fused-ring fused-ring heterocycle, etc., including but not limited to quinazolinyl, benzopyrazinyl, oxadiazolyl, benzothiopheneyl, phenanthiopheneyl, pyridyl, 1,10-phenantholinyl, pyrimidinyl, mesazinyl, and quinolinyl. The substituents of the heteroaryl group can be 1-3, and the substituents are arbitrarily selected from halogens, alkyl, phenyl, biphenyl, pyridyl, naphthyl, quinazolinyl, benzopyrazinyl, triazolyl, oxadiazolyl, and benzimidazolyl. The hydrogens on the substituents can be further substituted.

[0030] According to some embodiments of the present invention, in formula (I), ring 1, ring 2, ring 3, and ring 4 are each independently selected from a 5-membered unsaturated carbon ring, an aromatic ring having 6-30 carbon atoms, or a heteroaromatic ring having 3-30 carbon atoms. In some embodiments, ring 1, ring 2, ring 3, and ring 4 are each independently selected from an aromatic ring having 6-18 carbon atoms, or a heteroaromatic ring having 3-18 carbon atoms. In some embodiments, ring 1, ring 2, ring 3, and ring 4 are each independently selected from a benzene ring or a six-membered heteroaromatic ring. In some specific embodiments, ring 1, ring 2, ring 3, and ring 4 are each independently selected from a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a fluorene ring, a furan ring, a thiophene ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyran ring, a pyrrole ring, an imidazole ring, a pyrazole ring, an oxazole ring, a thiazole ring, a dibenzofuran ring, a dibenzothiophene ring, or a carbazole ring.

[0031] In some embodiments, at least two of rings 1, 2, 3, and 4 are selected from benzene rings. In some specific embodiments, any two of rings 1, 2, 3, and 4 are selected from benzene rings, or any three of rings 1, 2, 3, and 4 are selected from benzene rings, or all of rings 1, 2, 3, and 4 are benzene rings.

[0032] According to some embodiments of the present invention, T is selected from O, S, Se or NR. N In some preferred embodiments, T is 0. In some preferred embodiments, T is S.

[0033] According to some embodiments of the present invention, H in the first body material has the structure shown in formula (I-1):

[0034]

[0035] In equation (I-1), R X The definition of T is the same as that in equation (I).

[0036] In some preferred embodiments, in formula (I-1), R X It can be hydrogen, deuterium, halogen, alkyl group having 1-10 carbon atoms, cycloalkyl group having 3-10 carbon atoms, or aryl group having 6-18 carbon atoms. In some specific embodiments, in formula (I-1), R X It can be hydrogen, deuterium, fluorine, chlorine, bromine, iodine, methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, biphenyl, or naphthyl.

[0037] In some specific embodiments, the structure of H in the first host material is selected from the structures numbered H1 to H108, or the structure obtained by partially or completely replacing hydrogen with deuterium in any of the structures numbered H1 to H108; wherein the structures corresponding to H1 to H108 are as follows:

[0038]

[0039]

[0040]

[0041]

[0042] The asterisk (*) indicates the location where H and L are bonded.

[0043] According to some preferred embodiments of the present invention, L is connected to H and E respectively through two adjacent ring atoms on the arylene or heteroarylene ring.

[0044] According to some embodiments of the present invention, L has a structure selected from those represented by formula LM-1, formula LM-2, formula LM-3, formula LM-4, formula LM-5 or formula LM-6:

[0045]

[0046] Among them, A 1 A 2 A 3 A 4 A 5 and A 6Each occurrence may be the same or different, and each is independently selected from NR. L or CR L1 R L2 Each time Z appears, choose freely from O, S, Se, and SiR. a R b The group formed; R L1 and R L2 The definition is the same as R L R L The definition is the same as that described in equation (I);

[0047] The asterisk (*) indicates the location of the H and L bonds. This indicates the location of the E and L bonds.

[0048] In some preferred embodiments, L in the first body material is selected from the structure shown in formula LM-1 or formula LM-2 above.

[0049] In some preferred embodiments, in formula LM-1, A 1 To A 4 Each time it appears, it is selected from CR in the same or different ways. L1 R L2 In some preferred embodiments, in formula LM-2, A 1 To A 6 Each time it appears, it is selected from CR in the same or different ways. L1 R L2 .

[0050] In some embodiments, in formulas LM-1 to LM-6, R L R L1 and R L2 Each is independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-10 carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-10 carbon atoms, substituted or unsubstituted heterocycloalkyl groups having 3-10 carbon atoms, substituted or unsubstituted aralkyl groups having 7-18 carbon atoms, substituted or unsubstituted aryl groups having 6-18 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3-18 carbon atoms.

[0051] In some embodiments, the structure of L in the first host material is one of the structures numbered L-1 to L-40, or a structure obtained by partially or completely replacing hydrogen in any of the structures numbered L-1 to L-40 with deuterium; wherein the structures corresponding to L-1 to L-40 are as follows:

[0052]

[0053]

[0054] According to some embodiments of the present invention, E in the first body material is selected from the structure represented by formula (Ⅱ-1):

[0055]

[0056] Among them, Z1 to Z3 are each independently selected from NR N or CR a R b And at least two of Z1 to Z3 are NR. N ;R N R a and R b Define the same as equation (II);

[0057] Ar1 and Ar2 may be the same or different, and are each independently selected from substituted or unsubstituted aryl groups having 6-18 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3-18 carbon atoms. The substituents involved in Ar1 and Ar2 are selected from deuterium, halogens (e.g., fluorine, chlorine, bromine, iodine, etc.), cyano, alkyl groups having 1-10 carbon atoms (e.g., methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl, etc.), cycloalkyl groups having 3-10 carbon atoms (e.g., cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc.), aryl groups having 6-15 carbon atoms (e.g., phenyl, naphthyl, biphenyl, etc.), and combinations thereof.

[0058] In some preferred embodiments, in formula (Ⅱ-1), Z1 to Z3 are all NR. N .

[0059] In some implementations, R N Each occurrence, whether identical or different, is independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-10 carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-10 carbon atoms, substituted or unsubstituted heterocycloalkyl groups having 3-10 carbon atoms, substituted or unsubstituted aralkyl groups having 7-20 carbon atoms, substituted or unsubstituted alkoxy groups having 1-10 carbon atoms, substituted or unsubstituted aroxy groups having 6-20 carbon atoms, substituted or unsubstituted aryl groups having 6-20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-20 carbon atoms, and combinations thereof. In some preferred embodiments, R N It is hydrogen.

[0060] In some preferred embodiments, in formula (Ⅱ-1), Ar1 and Ar2 may be the same or different, and each is independently selected from the group consisting of: phenyl, deuterated phenyl, methyl phenyl, fluorophenyl, tert-butylphenyl, trideuterated methylphenyl, biphenyl, naphthyl, deuterated naphthyl, dibenzofuranyl, dibenzothiopheneyl, 9,9-dimethylfluorenyl, carbazolyl, pyridyl, pyrimidinyl, 4-cyanophenyl, 3-cyanophenyl, triphenylene.

[0061] In some preferred embodiments, Ar1 and Ar may be the same or different, and each is independently selected from the group consisting of:

[0062]

[0063] In some preferred embodiments, E in the first body material is selected from the structure represented by (Ⅱ-1-1):

[0064]

[0065] In formula (II-1-1), Ar1 and Ar2 are defined as in formula (II-1). In some embodiments, Ar1 and Ar2 in formula (II-1-1) are each independently selected from phenyl and dibenzofuranyl.

[0066] In some preferred embodiments, Ar1 and Ar2 are each independently selected from phenyl and dibenzofuranyl. In some specific embodiments, both Ar1 and Ar2 are phenyl. In some specific embodiments, Ar1 is phenyl and Ar2 is dibenzofuranyl.

[0067] In some preferred embodiments, the structure of E in the first host material is one of the structures shown in E1 to E44, or a structure obtained by partially or completely replacing hydrogen with deuterium in any of the structures shown in E1 to E44; wherein the structures corresponding to E1 to E44 are as follows:

[0068]

[0069]

[0070] In some embodiments, H in the first host material is selected from the group consisting of the structures shown in H1 to H108 above, L is selected from the group consisting of the structures shown in L-1 to L-40 above, and E is selected from the group consisting of the structures shown in E1 to E44 above. Optionally, the hydrogen in the compound is partially or completely replaced by deuterium.

[0071] In some embodiments, the first host material is selected from compounds numbered C1 to C600, or compounds obtained by partially or completely replacing hydrogen in any of the structures numbered C1 to C600 with deuterium. The structures shown in C1 to C600 have an HLE structure, where H, L, and E correspond to the following Table 1:

[0072] Table 1

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080] In some embodiments, the first body material has the structure shown in Formula A.

[0081]

[0082] In formula A, L is selected from phenylene or naphthylene, T is O or S, Ar1 and Ar2 are the same or different, and each is independently selected from phenyl, deuterated phenyl, methyl phenyl, fluorophenyl, tert-butylphenyl, trideuterated methylphenyl, dibenzofuranyl or dibenzothiophene.

[0083] In some implementations, in formula A, L is selected from...

[0084] In some implementations, Ar1 and Ar2 in formula A may be the same or different, and are each independently selected from...

[0085] According to some embodiments of the present invention, in formula (Ⅲ), HAr represents a substituted or unsubstituted C5-C containing one or more nitrogen atoms. 25 - Mixed aromatic compounds.

[0086] According to some embodiments of the present invention, in formula (Ⅲ), HAr represents an unsubstituted C5-C containing one or more nitrogen atoms. 25 - Heteroaryl groups and / or one or more (C6-C) 25 aryl-substituted C5-C 25- Heteroaryl. Specifically, HAr represents substituted or unsubstituted triazine, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted benzoisoquinolinyl, substituted or unsubstituted triazolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted naphridinyl, or substituted or unsubstituted benzothiophenepyrimidinyl. For example, HAr can represent substituted triazine, substituted pyrimidinyl, substituted quinoxalinyl, substituted quinazolinyl, or substituted naphridinyl. The substituents of these substituted triazine, substituted pyrimidinyl, substituted quinoxalinyl, substituted quinazolinyl, and substituted naphthinyl groups may be at least one of unsubstituted or diphenylamino groups, including phenyl, naphthyl, biphenyl, dimethylfluorenyl, dimethylbenzofluorenyl, dibenzothiopheneyl, dibenzofuranyl, benzonaphthothiopheneyl, phenylcarbazoyl, and phenylbenzocarbazoyl.

[0087] In some implementations, in formula (Ⅲ), L2 represents a single bond, substituted or unsubstituted C6-C. 25 aryl, substituted or unsubstituted C5-C 25 Hybrid aryl.

[0088] According to some embodiments of the present invention, in formula (Ⅲ), L2 represents a single bond, unsubstituted C6-C 18 Aromatic, unsubstituted C5-C 20 Heteroaryl groups. For example, L2 can represent a single bond, a phenylene group, or a pyridylene group.

[0089] In some implementations, in formula (Ⅲ), R1 represents substituted or unsubstituted C6-C. 30 Aryl, substituted or unsubstituted C5-C 25 Mixed aromatic compounds.

[0090] According to some embodiments of the present invention, in formula (Ⅲ), R1 represents unsubstituted or substituted by one or more (C1-C 10 ) alkyl and / or one or more (C6-C 18 aryl-substituted C6-C 29 aryl; or unsubstituted or substituted with one or more (C6-C) groups. 18 aryl-substituted C5-C 25 Heteroaryl. For example, R1 can be phenyl, naphthyl, phenylnaphthyl, biphenyl, dimethylfluorenyl, dimethylbenzofluorenyl, spirobisfluorenyl, spiro[fluorenyl-benzofluorenyl]yl, phenylcarbazolyl, phenylbenzocarbazolyl, dibenzofuranyl or dibenzothiophene.

[0091] In some embodiments, in formula (III), R2, R3, and R4 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C. 30 Alkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl, substituted or unsubstituted C3-C 30 cycloalkyl, substituted or unsubstituted C1-C 30 Alkoxy, substituted or unsubstituted tri(C1-C) 30 )alkylsilyl, substituted or unsubstituted di(C1-C2) 30 )alkyl (C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 )alkyl di(C6-C 30 arylsilyl, substituted or unsubstituted tri(C6-C) 30 ) arylsilyl, substituted or unsubstituted mono- or di-(C6-C) 30 )alkylamino, substituted or unsubstituted mono- or di-(C6-C) 30 ) arylamino or substituted or unsubstituted (C1-C 30 )alkyl (C6-C 30 Arylamino. Optionally, adjacent R2, R3, and R4 may be linked together to form one or more rings. For example, R2 to R4 may be hydrogen.

[0092] According to some embodiments of the invention, formula (Ⅲ) can be represented by any one of the following formulas (Ⅲ-1) and (Ⅲ-2).

[0093]

[0094] The definitions of X, Y, R1, R2, R3, R4, L2, b′, c′ and d′ are the same as in equation (Ⅲ).

[0095] Y1-Y5, Y 11 -Y 17 Each can be represented independently as N or CR. 15 .

[0096] According to a preferred embodiment of the present invention, at least one of Y1-Y5 represents CR. 15 And Y 11 To Y 17 At least one of them represents CR 15 .

[0097] According to some embodiments of the present invention, the R 15 Represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 Alkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl, substituted or unsubstituted C3-C 30 cycloalkyl, substituted or unsubstituted C1-C 30 Alkoxy, substituted or unsubstituted tri(C1-C) 30 )alkylsilyl, substituted or unsubstituted di(C1-C2) 30 )alkyl (C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 )alkyl di(C6-C 30 arylsilyl, substituted or unsubstituted tri(C6-C) 30 arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)alkylamino 30 ) arylamino or substituted or unsubstituted (C1-C 30 )alkyl (C6-C 30 One or more of the arylamino groups. Optionally, multiple R groups... 15 Adjacent elements can be connected to each other to form one or more loops.

[0098] According to some embodiments of the present invention, R 15 Indicates hydrogen, deuterium, substituted or unsubstituted C1-C 30 Alkyl, substituted or unsubstituted C6-C 25 Aryl, substituted or unsubstituted C5-C 25 One or more of the heteroaryl groups.

[0099] According to some embodiments of the present invention, R 15 Indicates hydrogen, deuterium, substituted or unsubstituted C6-C 18 Aryl groups, for example, are formed by one or more (C1-C) groups. 10 )alkyl and / or one or more di(C6-C) 18 )Arylamino-substituted C6-C 18 Aryl, or substituted or unsubstituted C5-C 20 Heteroaryl groups, for example, those formed by one or more (C6-C) groups. 18 One or more of the aryl-substituted heteroaryl groups.

[0100] According to some embodiments of the present invention, R 15It is selected from one or more of hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted dimethylbenzofluorenyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzonaphthothiopheneyl, substituted or unsubstituted phenylcarbazoyl, and substituted or unsubstituted phenylbenzocarbazoyl. For example, R 15 Each can independently represent hydrogen, unsubstituted or substituted phenyl, naphthyl, biphenyl, dimethylfluorenyl, dimethylbenzofluorenyl, dibenzothiopheneyl, dibenzofuranyl, benzonaphthothiopheneyl, phenylcarbazoyl or phenylbenzocarbazoyl.

[0101] According to some embodiments of the present invention, the second body material is selected from one or more of the following structures, but is not limited thereto:

[0102]

[0103]

[0104]

[0105]

[0106]

[0107] According to some embodiments of the present invention, the mass ratio of the first main material to the second main material is 1:(0.01-99), for example, 1:0.05, 1:0.1, 1:0.3, 1:0.5, 1:0.7, 1:1, 1:1.5, 1:2, 1:2.5, 1:3, 1:3.5, 1:4, 1:4.5, 1:5, 1:5.5, 1:6, 1:6.5, 1:7, 1:7.5, 1:8, 1:8.5, 1:9, 1:9.5, 1:10, 1:15, 1:20, 1:30, 1:40, 1:50, 1:60, 1:70, 1:80, 1:90 or any value between them.

[0108] In some embodiments, the mass ratio of the first main material to the second main material is 1:(0.1-9). In some embodiments, the mass ratio of the first main material to the second main material is 1:(0.4-2.5). In some embodiments, the mass ratio of the first main material to the second main material is 1:(0.6-1.5), for example, 1:(0.9-1.1).

[0109] A second aspect of the invention provides the use of the luminescent material composition described in the first aspect in an organic electroluminescent device. In some embodiments, the luminescent material composition is used as the host material of the luminescent layer in the organic electroluminescent device.

[0110] In some embodiments, a combination of at least one of compounds C1 to C600 from the first aspect of the present invention and at least one of compounds H2-1 to H2-76 can be used in an organic electroluminescent device from the second aspect of the present invention.

[0111] A third aspect of the present invention provides an OLED light-emitting layer comprising a host material and a dopant, wherein the host material comprises the composition described in the first aspect of the present invention.

[0112] According to some embodiments of the present invention, the dopant may comprise, but is not limited to, a compound represented by the following formula (Ⅳ).

[0113]

[0114] According to some embodiments of the present invention, in formula (Ⅳ), P is selected from the structures shown in formulas (P1) and (P2):

[0115]

[0116] Among them, R 100 To R 103 Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted C1-C. 30 Alkyl groups, such as unsubstituted or C1-C substituted with deuterium and / or one or more halogens. 30 Alkyl, substituted or unsubstituted C3-C 30 cycloalkyl, substituted or unsubstituted C6-C 30 Aryl, cyano, substituted or unsubstituted C3-C 30 heteroaryl or substituted or unsubstituted C1-C 30 Alkoxy; R 100 ~R 103 It can be connected to the adjacent R 100 To R 103 Together with the pyridine ring, it forms one or more rings, such as forming a substituted or unsubstituted quinoline, a substituted or unsubstituted benzofuranopyridine, a substituted or unsubstituted benzothiophenopyridine, a substituted or unsubstituted indenepyridine, a substituted or unsubstituted benzofuranoquinoline, a substituted or unsubstituted benzothiophenoquinoline, or a substituted or unsubstituted indenequinoline ring;

[0117] R 104 To R 107 Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted C1-C.30 Alkyl groups, for example, C1-C substituted with deuterium and / or one or more halogens. 30 Alkyl, substituted or unsubstituted C3-C 30 cycloalkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl, cyano, or substituted or unsubstituted C1-C 30 Alkoxy; R 104 To R 107 It can be connected to the adjacent R 104 To R 107 Together with the benzene ring, it forms one or more rings, such as substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted indenepyridine, substituted or unsubstituted benzofuranpyridine or substituted or unsubstituted benzothiophenepyridine ring;

[0118] R 201 To R 211 Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted C1-C. 30 Alkyl groups, for example, C1-C substituted with deuterium and / or one or more halogens. 30 Alkyl, substituted or unsubstituted C3-C 30 Cycloalkyl or substituted or unsubstituted C6-C 30 Aryl; R 201 To R 211 It can be connected to the adjacent R 201 To R 211 To form a ring;

[0119] n′ represents the integer 1, 2, or 3.

[0120] According to a specific embodiment of the present invention, the dopant compound is selected from any one of the following structures, but is not limited thereto.

[0121]

[0122]

[0123] A fourth aspect of the present invention provides an organic electroluminescent device comprising the light-emitting layer described in the third aspect of the present invention.

[0124] In some embodiments, the organic electroluminescent device includes an anode layer, a light-emitting layer, and a cathode layer.

[0125] In some embodiments, the light-emitting device further includes one or more of the following: a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

[0126] In some embodiments, the organic electroluminescent device includes an anode, a cathode, and at least one organic layer between the anode and the cathode. The organic layer may contain a plurality of host materials, including a compound represented by formula (HLE) as a first host material and a compound represented by formula (Ⅲ) as a second host material.

[0127] According to some embodiments of the present invention, an organic electroluminescent device includes an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, and at least one layer of the at least one light-emitting layer includes a compound represented by formula HLE and a compound represented by formula (Ⅲ).

[0128] According to some embodiments of the present invention, the light-emitting layer comprises a host, the host comprising a plurality of host materials, which may include a compound represented by formula HLE as a first host material among the plurality of host materials, and a compound represented by formula (III) as a second host material among the plurality of host materials. The weight ratio of the first host material to the second host material is in the range of about 1:99 to about 99:1, preferably about 10:90 to about 90:10, more preferably about 30:70 to about 70:30, and even more preferably about 40:60 to 60:40.

[0129] According to some embodiments of the present invention, the light-emitting layer is a layer that emits light, and may be a single layer or a multilayer consisting of two or more layers stacked together. Among the various host materials, the first host material and the second host material may be simultaneously contained in one layer or may be contained separately in different light-emitting layers.

[0130] According to some embodiments of the present invention, the doping concentration (mass percentage) of the dopant in the light-emitting layer is 1 wt% to 20 wt% relative to the host material in the light-emitting layer, preferably 1 wt% to 10 wt%, more preferably 2 wt% to 8 wt%.

[0131] According to some embodiments of the present invention, the organic electroluminescent device may further comprise at least one layer selected from the following: a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

[0132] According to some embodiments of the present invention, the organic electroluminescent device may further include, in addition to the various host materials of the present invention, at least one of the following: hole injection material, hole transport material, hole assist material, luminescent material, luminescent assist material, and electron blocking material.

[0133] According to some embodiments of the present invention, the organic electroluminescent device may further include at least one of azazine-based compounds, in addition to the various host materials of the present invention, as an electron transport material, an electron injection material, an electron buffer material, and a hole blocking material.

[0134] According to some embodiments of the present invention, the dopant included in the organic electroluminescent device of the present invention can be at least one phosphorescent or fluorescent dopant, preferably a phosphorescent dopant. The phosphorescent dopant material is not particularly limited, but can preferably be a metallized complex compound selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably a neighboring metallized complex compound selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably a neighboring iridium metallized complex compound.

[0135] In some embodiments, each layer of the organic electroluminescent device of the present invention can be obtained using dry film formation methods, such as vacuum evaporation, sputtering, plasma and ion plating methods, or wet film formation methods, such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating and flow coating methods.

[0136] When a solvent is used in a wet film formation method, a thin film can be formed by dissolving or diffusing the materials forming the layers into any suitable solvent (such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.). The solvent can be any solvent in which the materials forming the layers can be dissolved or diffused and in which there are no problems with film-forming capability.

[0137] According to some embodiments of the present invention, the compounds represented by formula HLE and the compounds represented by formula (III) can be film-formed by the methods listed above, typically by co-evaporation or mixed evaporation. Co-evaporation is a mixed deposition method in which two or more materials are placed in respective individual crucible sources and current is applied to two chambers simultaneously to evaporate the materials. Mixed evaporation is a mixed deposition method in which two or more materials are mixed in a crucible source prior to evaporation and current is applied to a chamber to evaporate the materials.

[0138] A fifth aspect of the present invention provides a display device or lighting device, including the organic electroluminescent device of the fourth aspect of the present invention.

[0139] This invention can provide a display system or lighting system by comprising multiple main materials. Additionally, it is possible to produce a display system or lighting system using the organic electroluminescent device of this invention.

[0140] In some embodiments, the display system is a display system for smartphones, tablets, laptops, PCs, TVs, or automobiles.

[0141] In some implementations, the lighting system is an outdoor or indoor lighting system.

[0142] The present invention has the following beneficial effects: the organic electroluminescent material composition provided by the present invention can be used to prepare organic electroluminescent devices with higher luminous efficiency and longer lifespan. Detailed Implementation

[0143] The invention will now be described in detail. However, the following description is intended to explain the invention and is not intended to limit the scope of the invention in any way.

[0144] definition

[0145] In this invention, the term "luminescent material" (also known as organic electroluminescent material) refers to a material that can be used in organic electroluminescent devices and may contain at least one compound. If desired, the organic electroluminescent material may be included in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole assist material, a luminescent assist material, an electron blocking material, a luminescent material (containing a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, and so on. In this invention, the term "multiple organic electroluminescent materials" refers to organic electroluminescent materials that can be included as a combination of at least two compounds in any layer constituting the organic electroluminescent device. It can mean both the material before being included in the organic electroluminescent device (e.g., before vapor deposition) and the material after being included in the organic electroluminescent device (e.g., after vapor deposition). For example, multiple organic electroluminescent materials can be combinations of at least two compounds, which can be contained in at least one of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron blocking layer, a light-emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. At least two compounds can be contained in the same or different layers by methods used in the art (e.g., co-evaporation or separate evaporation).

[0146] In this invention, the term "multiple host materials" refers to an organic electroluminescent material that is a combination of at least two host materials. It can refer to both materials included before (e.g., before vapor deposition) and materials included after (e.g., after vapor deposition) the organic electroluminescent device. The multiple host materials of this invention can be included in any light-emitting layer constituting the organic electroluminescent device. The at least two compounds included in the multiple host materials can be included simultaneously in one light-emitting layer, or they can be included separately in different light-emitting layers. If at least two host materials are included in one layer, they can, for example, be mixed and evaporated to form the layer, or they can be co-evaporated separately and simultaneously to form the layer.

[0147] In this invention, the term "C1-C" 30 "Alkyl" refers to a straight-chain or branched alkyl group having 1 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 1 to 10, and more preferably 1 to 6. The alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc. Here, the term "C3-C" is used... 30 "Cycloalkyl" refers to a mono- or polycyclic hydrocarbon having 3 to 30 carbon atoms in its cyclic skeleton, preferably 3 to 20, and more preferably 3 to 7. The cycloalkyl group may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.

[0148] The term "C3-C7 heterocyclic alkyl" refers to a cycloalkyl group having 3 to 7 cyclic skeleton atoms and including at least one heteroatom selected from the group consisting of B, N, O, S, SHI, and P, and preferably from the group consisting of O, S, and N. These heterocyclic alkyl groups may include tetrahydrofuran, pyrrolidine, thiopentan, tetrahydropyran, etc.

[0149] The term "C6-C" 30 "Aromatic" or "C6-C" 30 "Arylidene" refers to a monocyclic or fused-ring group derived from an aromatic hydrocarbon having 6 to 30 carbon atoms in its ring skeleton, preferably 6 to 20, more preferably 6 to 15. The aryl or arylidene groups may be partially saturated and may contain a spirostructure. The aryl groups may include phenyl, biphenyl, terphenyl, naphthyl, binatyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthrene, phenylphenanthrene, anthracene, indole, benzo[a]phenanthrene (trH1phenylenyl), pyrene, tetraphenyl, peryl, naphthacenyl, fluoranyl, spirobisfluorenyl, spiro[fluorenyl-benzo[a]fluorenyl], etc.

[0150] The term "C3-C" 50"Hybrid aryl" or "C3-C" 30 A "heteroaryl" is an aryl group having 3 to 50 or 3 to 30 ring skeleton atoms, wherein the number of carbon atoms in the ring skeleton is preferably 3 to 30, more preferably 5 to 20, and includes at least one (preferably 1 to 4) heteroatoms selected from the group consisting of B, N, O, S, Si, and P. The aforementioned heteroaryl or heteroarylene group can be a monocyclic or a fused ring condensed with at least one benzene ring; it can be partially saturated; it can be a heteroaryl or heteroarylene group formed by attaching at least one heteroaryl or aryl group to a heteroaryl group via one or more single bonds; and it can contain a spirostructure. The aforementioned heteroaryl groups can include monocyclic heteroaryl groups, such as furanyl, thiophene, pyrrole, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, etc. Isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetraazinyl, triazolyl, tetraazolyl, furazanyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc.; and fused-ring heteroaryl groups, such as benzofuranyl, benzothiopheneyl, isobenzofuranyl, dibenzofuranyl, benzonaphthofuranyl, dibenzothiopheneyl, benzonaphthothiopheneyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisooxazolyl, benzooxazolyl, isoindolyl, indolyl, inazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, quinoxolinyl, naphthinyl, carbazoleyl, benzocarbazoleyl, phenoxazinyl, phenanthinyl, phenanth-oxazolyl, benzom-dioxacyclopentenyl, etc.

[0151] In addition, "halogens" include F, Cl, Br and I.

[0152] The preparation method of the compounds of this invention is not limited, and they can be prepared by synthetic methods known to those skilled in the art. The following compounds are typical but not limited examples, and the synthesis of other compounds can be carried out by referring to this route.

[0153] Example 1: Synthesis of compound C1

[0154]

[0155] The synthesis route is as follows:

[0156]

[0157] Specific synthesis steps:

[0158] (1) In a 2L dry round-bottom flask, 10H-phenoloxazine (18.3g, 1eq, 100mmol), o-bromoiodobenzene (28.3g, 1eq, 100mmol), sodium tert-butoxide (14.4g, 1.5eq, 150mmol), Pd2(dba)3 (961mg, 0.01eq, 1mmol) and tri-tert-butylphosphine tetrafluoroborate (580mg, 0.02eq, 2mmol) were added sequentially. Nitrogen gas was replaced three times with toluene (200mL). The reaction was carried out at about 110℃ for 12 hours. After the reaction was completed, the temperature was lowered to room temperature and adjusted to neutral with 1M dilute hydrochloric acid. The mixture was allowed to stand and separated. The aqueous phase was extracted with toluene to separate the organic phase. The organic phases were combined and dried with anhydrous magnesium sulfate. After concentration, the mixture was separated by column chromatography to obtain a white solid compound H1-1 (23.6g, yield 70%).

[0159] (2) In a 2L dry round-bottom flask, H1-1 (33.7g, 1.0eq, 100mmol), triisopropyl borate (24.44g, 1.3eq, 130mmol) and tetrahydrofuran (400mL) were added dropwise. Under nitrogen protection, n-butyllithium (52mL, 1.3eq, 130mmol) was added dropwise at about -78℃, and the addition time was controlled to be about 1 hour. After the addition was completed, the temperature was controlled to be about -78℃ and the reaction was carried out for 1 hour. After the reaction was completed, the temperature was returned to 0℃ and dilute hydrochloric acid was added dropwise until the pH value was less than 3. The mixture was stirred for 10 minutes and extracted with ethyl acetate to separate the organic phase. The organic phase was washed three times with saturated sodium chloride solution and once with water. The organic phase was dried with anhydrous magnesium sulfate, concentrated and then slurried with heptane to obtain a white solid compound H1-2 (25.8g, yield 85%).

[0160] (3) In a 2L dry round-bottom flask, add H1-2 (30.3g, 1eq, 100mmol), potassium carbonate (27.6g, 2eq, 200mmol), 2-chloro-6-nitrophenyl trifluoromethanesulfonate (30.5g, 1eq, 100mmol), Pd(Ph3)4 (1.115mg, 0.01eq, 1mmol), toluene (320mL), water (160mL), and ethanol (160mL). Replace with nitrogen three times and react at about 75℃ for 12 hours. After the reaction is complete, cool to room temperature, extract with toluene, separate the organic phase, dry with anhydrous magnesium sulfate, concentrate and separate by column chromatography to obtain white solid compound H1-3 (18.6g, yield 45%).

[0161] (4) In a 2L dry round-bottom flask, add H1-3 (41.4g, 1eq, 100mmol), palladium acetate (830mg, 0.05eq, 5mmol), cesium carbonate (65.2g, 2eq, 200mmol), 100mL DMAc, and 400mL xylene to replace nitrogen three times. The reaction is carried out at about 75℃ for 12 hours. After the reaction is complete, the temperature is lowered to room temperature, and the organic phase is extracted with toluene. The organic phase is dried with anhydrous magnesium sulfate, concentrated, and separated by column chromatography to obtain a white solid compound H1-4 (24.6g, yield 65%).

[0162] (5) In a 2L dry round-bottom flask, add H1-4 (37.8g, 1eq, 100mmol), triphenylphosphine (78.6g, 3eq, 300mmol), and cesium carbonate (65.2g, 2eq, 200mmol) in sequence. The temperature is controlled at about 160℃ and the reaction is carried out for 5 hours. After the reaction is completed, the temperature is lowered to 100℃, 500mL of toluene is added, and after stirring, anhydrous zinc chloride (68g, 5eq, 500mmol) is added. The mixture is stirred for half an hour, filtered, and the filtrate is passed through a silica gel column. After desolvation in the column, ethanol is added and crystallization is carried out to obtain a yellow solid compound H1 (27.7g, yield 80%).

[0163] (6) In a 2L dry three-necked flask under nitrogen protection, 2-chloro-4,6-diphenyl-1,3,5-triazine (26.7g, 1.0eq, 100mmol), o-fluorophenylboronic acid (15.4g, 1.1eq, 110mmol), potassium carbonate (41.4g, 3.0eq, 300mmol), palladium 132 (45mg, 0.5g / mol), 400mL dioxane, and 200mL water were added sequentially. The mixture was heated to 100℃ and reacted for 12 hours. After the reaction was complete, the mixture was cooled to room temperature, filtered, and the bottom of the flask was washed with heptane. The resulting solid was dissolved in toluene at 100V, passed through a silica gel-alumina fast column, and washed with toluene until the filtrate showed no fluorescence. The filtrate was concentrated to at least the amount of solvent and filtered to obtain E1-1 (27.8g, yield 85%).

[0164] (7) H1 (34.6 g, 1.1 eq, 100 mmol), E1-1 (36.0 g, 1 eq, 110 mmol), cesium carbonate (65.2 g, 2 eq, 200 mmol), and 400 mL DMAc were added sequentially to a 2 L dry round-bottom flask. The mixture was reacted at approximately 160 °C for 12 hours. After the reaction was completed, the mixture was cooled to room temperature. 200 mL of water and 500 mL of dichloromethane were added to the system. The mixture was separated by dichloromethane extraction of the aqueous phase. The organic phase was then separated and dried with anhydrous magnesium sulfate. After concentration, the organic phase was separated by column chromatography to obtain a white solid compound C1 (32.7 g, yield 50%).

[0165] Product MS (m / e): 653.

[0166] 1 H NMR (400MHz, CDCl3): δ8.45–8.36(m,4H),8.06(dd,1H),7.97(dd,1H),7.72–7.64(m,2H),7.59(dd,1H),7.5 6–7.45(m,9H),7.44(ddd,1H),7.39(t,1H),7.32(dd,1H),7.30–7.22(m,3H),7.15(ddd,1H),6.92(ddd,2H).

[0167] Example 2: Synthesis of compound C55

[0168]

[0169] The synthesis route is as follows:

[0170]

[0171] Specific synthesis steps:

[0172] By replacing 10H-phenoloxazine with 10H-phenathiazine, selecting an appropriate material ratio, and keeping other raw materials and steps the same as in Example 1, compound C55 was obtained.

[0173] Product MS (m / e): 380.

[0174] 1 H NMR (400MHz, CDCl3): δ8.45-8.36(m,4H),7.97(dd,1H),7.76-7.67(m,3H),7.59(dd,1H),7.56-7.45(m,7H),

[0175] 7.48-7.38(m,5H),7.34-7.30(dddd,4H),7.27(dd,1H),7.18(td,1H).

[0176] Example 3: Synthesis of compound C109

[0177]

[0178] The synthesis route is as follows:

[0179]

[0180] By replacing o-fluorophenylboronic acid with (8-fluoronaphth-1-yl)boronic acid and selecting an appropriate material ratio, while keeping all other raw materials and steps the same as in Example 1, compound C109 was obtained. Product MS (m / e): 703.

[0181] Example 4: Synthesis of compound C163

[0182]

[0183] The synthesis route is as follows:

[0184]

[0185] Specific synthesis steps:

[0186] In a 2L dry round-bottom flask, H55 (36.2 g, 1.1 eq, 100 mmol), E1-2 (41.5 g, 1 eq, 110 mmol), cesium carbonate (65.2 g, 2 eq, 200 mmol), and 400 mL DMAc were added sequentially. The mixture was reacted at approximately 160 °C for 12 hours. After the reaction was complete, the mixture was cooled to room temperature, and 200 mL of water and 500 mL of dichloromethane were added. The mixture was separated by dichloromethane extraction of the aqueous phase, and the organic phase was dried over anhydrous magnesium sulfate. After concentration, column chromatography was used to obtain a white solid compound C163 (32.3 g, 46% yield). MS (m / e) of the product: 719.

[0187] Example 5: Synthesis of compound C217

[0188]

[0189] The synthesis route is as follows:

[0190]

[0191] Specific synthesis steps:

[0192] (1) Add 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (63.5 g, 1 eq., 177 mmol), o-fluorophenylboronic acid (25.6 g, 1.03 eq., 183 mmol), potassium carbonate (30.42 g, 3 eq., 93.3 mmol), Pd(PPh3)4 (2.05 g, 0.01 eq., 1.77 mmol), and dioxane 50 to a 1 L three-necked flask. 0 mL of water and 265 mL of nitrogen were added, and the mixture was heated to 100 °C and refluxed for 3 h. The reaction was monitored until it was complete. The mixture was then cooled to room temperature, and 500 mL of water was added and stirred for 0.5 h. The mixture was filtered, and the resulting solid was dissolved in 500 mL of dichloromethane. The organic phase was passed through a vacuum column (5 cm silica gel - 3 cm alumina - 2 cm anhydrous sodium sulfate) and eluted with dichloromethane until no product spot was observed. The solvent was then removed, and 2 times the volume of toluene was added. The mixture was heated to 110 °C to dissolve, cooled to crystallize, and filtered to obtain 65.6 g of E16-1, with a yield of 88%.

[0193] (2) In a 2L dry round-bottom flask, H1 (34.6g, 1.1eq, 100mmol), E16-1 (45.9g, 1eq, 110mmol), cesium carbonate (65.2g, 2eq, 200mmol), and 400mL DMAc were added sequentially. The reaction was carried out at a temperature of about 160℃ for 12 hours. After the reaction was completed, the temperature was lowered to room temperature, and 200mL of water and 500mL of dichloromethane were added to the system. The mixture was separated, and the aqueous phase was extracted with dichloromethane to separate the organic phase. The organic phase was dried with anhydrous magnesium sulfate, concentrated, and separated by column chromatography to obtain a white solid compound C217 (37.9g, yield 51%).

[0194] Product MS (m / e): 743.

[0195] 1 H NMR (400MHz, CDCl3): δ8.44-8.37(m,2H),7.98(ddd,2H),7.84(dd,1H),7.72-7.64(m,2H), 7.66-7.56(m,4H),7.56-7.41(m,9H),7.39-7.23(m,5H),7.18-7.11(m,2H),6.92(ddd,2H).

[0196] Example 6: Synthesis of compound C271

[0197]

[0198] The synthesis route is as follows:

[0199]

[0200] Specific synthesis steps:

[0201] In a 2L dry round-bottom flask, H55 (36.2 g, 1.1 eq, 100 mmol), E16-1 (45.9 g, 1 eq, 110 mmol), cesium carbonate (65.2 g, 2 eq, 200 mmol), and 400 mL DMAc were added sequentially. The mixture was reacted at approximately 160 °C for 12 hours. After the reaction was complete, the mixture was cooled to room temperature, and 200 mL of water and 500 mL of dichloromethane were added. The mixture was separated by dichloromethane extraction of the aqueous phase, and the organic phase was dried over anhydrous magnesium sulfate. After concentration, column chromatography was used to obtain a white solid compound C271 (41.7 g, 55% yield). MS (m / e) of the product: 759.

[0202] Example 7: Synthesis of compound C325

[0203]

[0204] The synthesis route is as follows:

[0205]

[0206] Specific synthesis steps:

[0207] By replacing o-fluorophenylboronic acid with (8-fluoronaphth-1-yl)boronic acid and selecting an appropriate material ratio, while keeping all other raw materials and steps the same as in Example 5, compound C325 was obtained. MS (m / e) of the product: 793.

[0208] Example 8: Synthesis of compound C379

[0209]

[0210] The synthesis route is as follows:

[0211]

[0212] Specific synthesis steps:

[0213] By replacing E16-1 with E16-2 and selecting a suitable material ratio, while keeping all other raw materials and steps the same as in Example 6, compound C379 was obtained. Product MS (m / e): 809.

[0214] Compounds H2-1, H2-3, H2-6, H2-26, H2-52, H2-68, H2-70, and H2-72 can be prepared by synthetic methods known to those skilled in the art. For example, they can be prepared by referring to Korean Patent Application Publication No. 2017-0022865A (published on March 2, 2017).

[0215]

[0216] The luminous efficiency and lifetime characteristics of the OLED according to this disclosure will be explained below. However, the following examples only illustrate the characteristics of the OLED according to this disclosure, and this disclosure is not limited to the following examples.

[0217] Device Example 1: OLED-1

[0218] The structure of the device of the present invention is as follows: ITO / HI(10nm) / HT01(60nm) / EB(5nm) / First body: Second body:D-2(49%:49%:2%) / (40nm) / HB(10nm) / ET01:LiQ(1:1)(30nm) / LiQ(1nm) / Al.

[0219] The specific preparation process is as follows:

[0220] (1) The glass plate coated with ITO transparent conductive layer was ultrasonically treated in commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in acetone: ethanol mixed solvent (volume ratio 1:1), baked in a clean environment until the moisture was completely removed, cleaned with ultraviolet light and ozone, and bombarded with low-energy cation beam.

[0221] (2) Place the glass substrate with the anode into the vacuum chamber and evacuate to 1×10⁻⁶. -5 ~9×10 -3 Pa, HI is vacuum-deposited as a hole injection layer on the above-mentioned anode layer film at a deposition rate of 0.1 nm / s and a total film thickness of 10 nm; then the first hole layer HT01 is deposited at a deposition rate of 0.1 nm / s and a thickness of 60 nm; then the electron blocking layer EB is deposited at a deposition rate of 0.1 nm / s and a film thickness of 5 nm.

[0222] (3) An EML is vacuum-deposited on the hole transport layer as the light-emitting layer of the device. The EML includes a first host compound C1, a second host compound H2-1, and a dopant compound D-2, with a mass percentage of 49%:49%:2%. The first and second host compounds are co-evaporated to form the organic light-emitting layer of the device. The evaporation rate is 0.1 nm / s, and the total film thickness is 40 nm. Then, 10 nm of HB is evaporated to form a hole blocking layer. The evaporation rate is 0.1 nm / s.

[0223] (4) ETO1:LiQ with a mass ratio of 1:1 was deposited on the hole blocking layer as the electron transport material of the device electron transport layer. The deposition rate was 0.1 nm / s and the total film thickness was 30 nm.

[0224] (5) A 1 nm thick LiQ layer was vacuum-deposited on the electron transport layer as an electron injection layer, and a 150 nm thick Al layer was deposited as the cathode of the device. After encapsulation, the OLED-1 device was obtained.

[0225] Devices OLED-2 to OLED-4: The mass mixing ratio of the first host material and the second host material was adjusted, and the other layers were the same as in device embodiment 1, to obtain OLED-2 to OLED-4 devices respectively.

[0226] Devices OLED-5 to OLED-11: Different host materials were used, and the specific compounds are shown in Table 2. The other layers were the same as in Device Example 1, and OLED-5 to OLED-11 devices were obtained respectively.

[0227] Comparative devices OLED-1 and OLED-2: Using a single host, with C1 and H2-1 as the host compounds respectively, and the same as in device example 1, comparative devices OLED-1 and OLED-2 were prepared.

[0228] Comparative device OLED-3: Using a single host compound, with comparative compound P72 as the host compound, and other aspects being the same as in device example 1, comparative device OLED-3 was prepared.

[0229] Comparative device OLED-4: C1 and P72 were mixed in a 1:1 mass ratio as the main materials, and the other layers were the same as in device example 1 to prepare the comparative device OLED-4.

[0230] The molecular structures of each functional layer material are as follows:

[0231]

[0232] The device prepared above was subjected to performance testing, with a brightness of 5000 cd / m². 2 Under the given conditions, the performance test results of each device are detailed in Table 2.

[0233] Table 2

[0234]

[0235] Table 2 confirms that for devices OLED-1 to OLED-4, varying the mixing ratio of the host materials results in the highest efficiency and lifetime when the mixing ratio is 50%:50%. Compared to comparative devices 1-4, OLED-1, OLED-5 to OLED-11, organic electroluminescent devices containing specific compound combinations according to the present invention as host materials exhibit higher luminous efficiency and / or longer lifetime characteristics than organic electroluminescent devices with a single host material.

[0236] Although the present invention has been described in detail above with general descriptions, specific embodiments, and experiments, it is not intended to limit the scope of the invention, as will be obvious to those skilled in the art. Therefore, any modifications or improvements made without departing from the spirit of the invention are within the scope of protection claimed by the present invention.

Claims

1. A luminescent material composition comprising a first host material and a second host material, wherein, The first main material has a structure represented by formula HLE, where H has a structure represented by formula (I-1): Equation (I-1) In formula (I-1), T is selected from O, S, or Se; R X Each occurrence, whether identical or different, indicates monosubstituted, polysubstituted, or unsubstituted. R X It can be hydrogen, deuterium, halogen, or an alkyl group having 1-10 carbon atoms; 、 、 、 ； L has the structure corresponding to L-1, L-2, L-3 or L-40, or the structure obtained by partially or completely replacing the hydrogen in any of the structures shown in L-1, L-2, L-3 or L-40 with deuterium; "Indicates the location of the H and L bonds," "Indicates the location of the E and L bond; E has the structure represented by equation (II-1-1): Equation (Ⅱ-1-1) In formula (II-1-1), Ar1 and Ar2 may be the same or different, and each is independently selected from the group consisting of the following groups: phenyl, deuterated phenyl, methyl phenyl, fluorophenyl, tert-butylphenyl, trideuterated methylphenyl, biphenyl, naphthyl, deuterated naphthyl, dibenzofuranyl, dibenzothiopheneyl, 9,9-dimethylfluorenyl, carbazolyl, pyridyl, pyrimidinyl, 4-cyanophenyl, 3-cyanophenyl, triphenylene; The second main material has a structure as shown in formula (Ⅲ): Formula (III) In equation (Ⅲ), X and Y are each independently selected from -N= and -NR=. 10 -, -O-, or -S-, where X represents -N= and Y represents -NR. 11 -, -O-, or -S-, or when X represents -NR 10 When -, Y represents -N=, -O-, or -S-; HAr is selected from substituted or unsubstituted C3-C atoms containing one or more nitrogen atoms. 30 The heteroaryl group may have 1 to 3 substituents, wherein the substituents are arbitrarily selected from halogens, alkyl groups, phenyl groups, biphenyl groups, pyridyl groups, naphthyl groups, quinazolinyl groups, benzopyrazinyl groups, triazolyl groups, oxadiazolyl groups, and benzimidazolyl groups; L2 is selected from single-bonded, unsubstituted C6-C. 30 aryl, unsubstituted C3-C 30 heteroaryl; R1 is selected from phenyl, naphthyl, phenylnaphthyl, biphenyl, dimethylfluorenyl, dimethylbenzofluorenyl, spirobisfluorenyl, spiro[fluorenyl-benzofluorenyl]yl, phenylcarbazolyl, phenylbenzocarbazolyl, dibenzofuranyl or dibenzothiopheneyl; R2, R3, and R4 are each independently selected from hydrogen and deuterium; R 10 and R 11 Each is independently selected from hydrogen, deuterium, and unsubstituted C1-C. 30 Alkyl, substituted or unsubstituted C6-C 30 Aryl, the substituents of which can be alkyl, halogen or phenyl; b′ and c′ are each independently selected from 1 or 2; d′ is selected from 1, 2, 3 or 4; when b′, c′ and d′ are greater than 1, each of R2, R3 and R4 is the same or different.

2. The luminescent material composition according to claim 1, characterized in that, E is selected from the structure represented by equation (Ⅱ-1-1): Equation (Ⅱ-1-1) Ar1 and Ar2 are each independently selected from phenyl and dibenzofuranyl.

3. The luminescent material composition according to claim 1, characterized in that, In the first main material, The structure of H is selected from the structures shown in H1, H51-H55, and H105-H108, or the structure obtained by partially or completely replacing hydrogen with deuterium in any of the structures shown in H1, H51-H55, and H105-H108; wherein the structures corresponding to H1, H51-H55, and H105-H108 are as follows: , , , , , , , , , ; and / or The structure L is one of the structures shown in L-1, L-2, L-3, and L-40, or a structure obtained by partially or completely replacing the hydrogen in any of the structures shown in L-1, L-2, L-3, and L-40 with deuterium; wherein the structures corresponding to L-1, L-2, L-3, and L-40 are as follows: , , , ; and / or Structure E is one of the structures shown in E1 to E44, or a structure obtained by partially or completely replacing the hydrogen in any of the structures shown in E1 to E44 with deuterium; wherein the structures corresponding to E1 to E44 are as follows: 。 4. The luminescent material composition according to claim 3, characterized in that, In the first host material, H is selected from the group consisting of the structures shown in H1, H51-H55 and H105-108 as described in claim 3; L is selected from the group consisting of the structures shown in L-1, L-2, L-3 and L-40 as described in claim 3; and E is selected from the group consisting of the structures shown in E-1 to E-44 as described in claim 3. Optionally, the hydrogen in the first host material is partially or completely replaced by deuterium.

5. The luminescent material composition according to claim 3, characterized in that, The first host material is selected from compounds numbered C1, C51-C55, C105-C109, C159-C163, C213-C217, C267-C271, C321-C325, C375-C379, and C429-C600, or compounds obtained by partially or completely replacing hydrogen with deuterium in any of the structures corresponding to C1, C51-C55, C105-C109, C159-C163, C213-C217, C267-C271, C321-C325, C375-C379, and C429-C600. 。 6. The luminescent material composition according to claim 1, characterized in that, The second main material has a structure as shown in formula (Ⅲ-1) or formula (Ⅲ-2): Equation (Ⅲ-1) Equation (Ⅲ-2) The definitions of X, Y, R1, R2, R3, R4, L2, b′, c′ and d′ are the same as in equation (Ⅲ); Y1 to Y5, Y 11 To Y 17 Each is independently selected from N or CR 15 ; At least one of Y1 to Y5 is selected from CR 15 And Y 11 To Y 17 At least one of them is selected from CR 15 ; The R 15 It is selected from hydrogen, deuterium, unsubstituted or substituted with one or more diphenylamino groups, phenyl, naphthyl, biphenyl, dimethylfluorenyl, dimethylbenzofluorenyl, dibenzothiopheneyl, dibenzofuranyl, benzonaphthothiopheneyl, phenylcarbazolyl or phenylbenzocarbazolyl.

7. The luminescent material composition according to claim 6, characterized in that, The second host material is selected from the group consisting of the following compounds: 。 8. The luminescent material composition according to claim 1, characterized in that, The mass ratio of the first main material to the second main material is 1:(0.1-9).

9. The luminescent material composition according to claim 1, characterized in that, The mass ratio of the first main material to the second main material is 1:(0.4-2.5).

10. The luminescent material composition according to claim 1, characterized in that, The mass ratio of the first main material to the second main material is 1:(0.6-1.5).

11. The luminescent material composition according to claim 1, characterized in that, The mass ratio of the first main material to the second main material is 1:(0.9-1.1).

12. The use of the luminescent material composition according to any one of claims 1-11 in an organic electroluminescent device, characterized in that, The luminescent material composition is used as the host material of the luminescent layer in organic electroluminescent devices.

13. An OLED light-emitting layer comprising a host material and a dopant, wherein the host material comprises the light-emitting material composition according to any one of claims 1-11.

14. An organic electroluminescent device comprising the light-emitting layer of claim 13.

15. The organic electroluminescent device according to claim 14, characterized in that, The organic electroluminescent device includes an anode layer, a light-emitting layer, and a cathode layer.

16. The organic electroluminescent device according to claim 15, characterized in that, The electroluminescent device further includes one or more of the following: hole injection layer, hole transport layer, electron blocking layer, light emission layer, hole blocking layer, electron transport layer, and electron injection layer.

17. A display component comprising the organic electroluminescent device according to any one of claims 14 to 16.

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