CN112358868A - Organic electroluminescent composition and application thereof - Google Patents

Organic electroluminescent composition and application thereof Download PDF

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CN112358868A
CN112358868A CN202011131958.6A CN202011131958A CN112358868A CN 112358868 A CN112358868 A CN 112358868A CN 202011131958 A CN202011131958 A CN 202011131958A CN 112358868 A CN112358868 A CN 112358868A
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organic electroluminescent
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CN112358868B (en
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陈志宽
李祥智
蔡烨
魏定纬
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Ningbo Lumilan New Material Co ltd
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Abstract

The invention provides an organic electroluminescent composition and application thereof, wherein the organic electroluminescent composition comprises a compound A and a compound B, the temperature difference of the thermal decomposition temperatures of the compound A and the compound B is within 20 ℃, and the compound A has a structure shown as a formula I. The organic electroluminescent composition of the present invention enables organic optoelectronic devices to achieve high efficiency and long lifetime.

Description

Organic electroluminescent composition and application thereof
Technical Field
The invention belongs to the technical field of organic electroluminescent materials, and relates to an organic electroluminescent composition and application thereof.
Background
As the demand for flat panel displays increases, Organic Light Emitting Diodes (OLEDs) have recently attracted attention. The organic light emitting diode converts electric energy into light by applying current to an organic light emitting material, and the performance of the organic light emitting diode is affected by an organic material disposed between electrodes.
Currently, 4,4 '-N, N' -dicarbazole-biphenyl (CBP) is the most well known phosphorescent host material. While CBP materials provide good luminescent characteristics, they have the following disadvantages: (1) they are less thermally stable and they may degrade during the high temperature deposition process in vacuum, resulting in a reduced lifetime of the device. (2) The power efficiency of the organic electroluminescent device is obtained by [ (pi/voltage) × current efficiency ], and the power efficiency is inversely proportional to the voltage. Although the organic electroluminescent device including the phosphorescent host material provides higher current efficiency (cd/a) than the organic electroluminescent device including the fluorescent material, a considerably high driving voltage is required. Therefore, there is no advantage in power efficiency (lm/W).
To improve the luminous efficiency, driving voltage and/or lifetime, the concept of using a multi-host light emitting material has been proposed. However, they are not satisfactorily put into practical use.
Disclosure of Invention
In view of the defects of the prior art, the invention aims to provide an organic electroluminescent composition and application thereof. Organic electroluminescent composition of the present invention
In order to achieve the purpose, the invention adopts the following technical scheme:
in one aspect, the present invention provides an organic electroluminescent composition, including a compound a and a compound B, where a thermal decomposition temperature difference between the compound a and the compound B is within 20 degrees celsius, and the compound a has a structure shown in formula I below:
Figure BDA0002735445750000011
wherein, Y1And Y2Each independently selected from the group consisting of single bond, N, CR11The oxygen, the oxygen or the sulfur is selected from the group consisting of O and S,
R1-R9、R11each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10Alkyl, substituted or unsubstituted C1-C10Cycloalkyl, substituted or unsubstituted C2-C10Alkenyl of, substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C3-C30Heteroaryl of (3), LOR12、LSR12、LNR13R14Or LSi R15 R16R17，
R1-R9、R11Each independently exists or 2-4 adjacent groups are connected into a ring X through chemical bonds,
R12-R17each independently selected from hydrogen, substituted or unsubstituted C1-C10Alkyl, substituted or unsubstituted C1-C10Cycloalkyl, substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C3-C30Heteroaryl of (a), a plurality of R12The radicals being identical or different, R13And R14Are not connected or connected to form a ring C,
L、L1each independently selected from a single bond, substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C3-C30Ar is selected from substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C3-C30The heteroaryl group of (a);
n is an integer of 1 to 2.
The substituents are each independently selected from halogen, cyano, nitro, substituted with at least one R20Substituted or unsubstituted groups as follows: one of C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkenyl, C6-C30 aryl, C6-C30 aryloxy, C6-C30 thioaryloxy, C6-C30 arylamine, C3-C30 heteroaryl, C3-C30 heteroarylamine, or a combination of these systems;
R20selected from deuterium, cyano, nitro, halogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, methoxy, ethoxy, propoxy, phenyl, biphenyl, naphthyl, anthryl or phenanthryl.
In the invention, the compound A has a condensed ring structure formed by four rings shown in a formula I, a mother nucleus has good electron mobility, an N-containing heterocyclic substituent is introduced at a specific position of the mother nucleus, so that the electron mobility in the direction of the diffusion effect of LUMO electron cloud can be increased, the stability of the compound can be increased, and the faster electron transport characteristic is shown at the same time.
In the present invention, the thermal decomposition temperature difference between the compound a and the compound B is within 20 degrees celsius, and for example, may be 20 degrees celsius, 18 degrees celsius, 15 degrees celsius, 13 degrees celsius, 10 degrees celsius, 8 degrees celsius, 5 degrees celsius, 3 degrees celsius, 1 degree celsius, or the like.
Preferably, the compound a has the structure shown in formula II below:
Figure BDA0002735445750000031
wherein, X1-X5Each independently selected from N or CR10And at least one is N;
R10selected from hydrogen, deuterium, halogen, cyano, substituted by at least one R20Substituted with the following groups: C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkenyl, C6-C30 aryl, C6-C30 aryloxy, C6-C30 thioaryloxy, C6-C30 arylamine, C3-C30 heteroaryl, C3-C30 heteroarylamine, or the combination of these systems, and adjacent R10Are not connected or connected into a ring W;
Y1、Y2、R1-R9、L1is as defined in formula I;
preferably, X1-X52-3 of them are N;
preferably, ring W is substituted by at least one R20Substituted or unsubstituted groups as follows: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, benzothiophene ring, benzofuran ring, indene ring and indole ring.
Further preferably, the compound A is any one of the following compounds II-1 to II-3:
II-1：
Figure BDA0002735445750000032
II-2：
Figure BDA0002735445750000033
II-3：
Figure BDA0002735445750000034
wherein, Y1、Y2、R1-R9、L1Is as defined in formula I, R10Is as defined in formula II,
Figure BDA0002735445750000041
indicates that two adjacent R10 are connected into a ring;
preferably, Y1Is N, Y2Is CR11；
Preferably, Y2Is N, Y1Is CR11。
Preferably, Y1And Y2Are all N.
Preferably, said Y is1And Y2At least one is a single bond.
Preferably, said Y is1Is O, Y2Is a single bond, or Y2Is O, Y1Is a single bond;
preferably, said Y is1Is S, Y2Is a single bond, or Y2Is S, Y1Is a single bond, and is a single bond,
preferably, said Y is1Is N, Y2Is a single bond, or Y2Is N, Y1Is a single bond, and is a single bond,
preferably, said Y is1Is CR11，Y2Is a single bond, or Y2Is CR11，Y1Is a single bond.
Preferably, the compound A is any one of the following compounds A-1 to A-64, A '-1 to A' -64 and A '-1 to A' -24:
Figure BDA0002735445750000042
Figure BDA0002735445750000051
Figure BDA0002735445750000061
Figure BDA0002735445750000071
Figure BDA0002735445750000081
Figure BDA0002735445750000091
Figure BDA0002735445750000101
Figure BDA0002735445750000111
Figure BDA0002735445750000121
preferably, the compound B is a carbazole-based compound.
Preferably, the compound B has the structure shown in formula III below:
Figure BDA0002735445750000122
wherein L is2-L4Each of which isIndependently selected from single bonds, by at least one R20Substituted or unsubstituted C6-C30Aryl of (a) by at least one R20Substituted or unsubstituted C3-C30The heteroaryl group of (a);
Ar3selected from the group consisting of20Substituted or unsubstituted C6-C30Aryl of (a) by at least one R20Substituted or unsubstituted C3-C30Heteroaryl of (2), NR13R14，
m is an integer of 1-2, m1 is an integer of 0-4, m2 is an integer of 0-4, n1 is an integer of 1-2, n2 is an integer of 1-2; l is3Is a single bond, n1 is 1; l is4Is a single bond, n2 is 1;
R18-R19each independently selected from deuterium, halogen, cyano, substituted with at least one R20Substituted or unsubstituted C1-C10By at least one R20Substituted or unsubstituted C1-C10By at least one R20Substituted or unsubstituted C2-C10By at least one R20Substituted or unsubstituted C6-C30Aryl of (a) by at least one R20Substituted or unsubstituted C3-C30Heteroaryl of (A), OR12、SR12、NR13R14；
n1 Xm 1R18Identical or different, n2 Xm 2R19The same or different;
when m1 is 2 or more, R18Independently exist or are adjacent to each other to form a ring;
when m2 is 2 or more, R19 may be present alone or form a ring adjacent to each other.
Preferably, the compound B has the structure shown in formula IV below:
Figure BDA0002735445750000131
wherein L is2-L4、R18-R19、Ar3M, m2, n1 and n2 are defined by formula III is defined as1Selected from O, S, NL5Ar5、CR21R22；
Ar5Selected from the group consisting of20Substituted or unsubstituted C6-C30Aryl of (a) by at least one R20Substituted or unsubstituted C3-C30Heteroaryl of (2), NR13R14，
L5Selected from single bonds, by at least one R20Substituted or unsubstituted C6-C30Aryl of (a) by at least one R20Substituted or unsubstituted C3-C30The heteroaryl group of (a) is a group,
R21、R22each independently hydrogen, by at least one R20Substituted or unsubstituted C1-C10By at least one R20Substituted or unsubstituted C1-C10By at least one R20Substituted or unsubstituted C6-C30Aryl of (a) by at least one R20Substituted or unsubstituted C3-C30The heteroaryl group of (a);
R21、R22either alone or linked to form a spiro ring.
m3 is an integer from 0 to 4 (e.g., 0, 1, 2, 3, or 4), n3 is an integer from 1 to 2, and m1 is an integer from 0 to 2.
Preferably, the compound B has the structure shown in formula V below:
Figure BDA0002735445750000132
wherein L is2-L4、R18-R19、Ar3M, m1, m2, m3, n1, n2 and n3 are as defined in formula IV;
Z2selected from O, S, NL5Ar5、CR21R22；
Ar5Selected from the group consisting of20Substituted or unsubstituted C6-C30Aryl of (a) by at least one R20Substituted or unsubstituted C3-C30Heteroaryl of (2), NR13R14，
L5Selected from single bonds, by at least one R20Substituted or unsubstituted C6-C30Aryl of (a) by at least one R20Substituted or unsubstituted C3-C30The heteroaryl group of (a) is a group,
R21、R22each hydrogen, by at least one R20Substituted or unsubstituted C1-C10By at least one R20Substituted or unsubstituted C1-C10By at least one R20Substituted or unsubstituted C6-C30Aryl of (a) by at least one R20Substituted or unsubstituted C3-C30The heteroaryl group of (a);
R21、R22either alone or linked to form a spiro ring.
Preferably, Ar3、Ar5Each independently selected from the group consisting of20Substituted or unsubstituted phenyl, substituted or unsubstituted by at least one R20Substituted or unsubstituted biphenyl, substituted or unsubstituted biphenyl with at least one R20Substituted or unsubstituted terphenyl group substituted by at least one R20Substituted or unsubstituted naphthyl, substituted by at least one R20Substituted or unsubstituted anthracenyl, by at least one R20Substituted or unsubstituted triphenylene, substituted or unsubstituted with at least one R20Substituted or unsubstituted pyridyl, substituted or unsubstituted with at least one R20Substituted or unsubstituted dibenzothienyl by at least one R20Substituted or unsubstituted dibenzofuranyl, by at least one R20Substituted or unsubstituted carbazolyl, with at least one R20Substituted or unsubstituted fluorenyl, NR13R14Or a combination thereof,
R13、R14each independently selected from the group consisting of20Substituted or unsubstituted phenyl, substituted or unsubstituted by at least one R20Substituted or unsubstituted biphenyl, substituted or unsubstituted biphenyl with at least one R20Substituted or unsubstituted terphenyl group substituted by at least one R20Substituted or unsubstituted naphthyl,By at least one R20Substituted or unsubstituted anthracenyl, by at least one R20Substituted or unsubstituted triphenylene, substituted or unsubstituted with at least one R20Substituted or unsubstituted pyridyl, substituted or unsubstituted with at least one R20Substituted or unsubstituted dibenzothienyl by at least one R20Substituted or unsubstituted benzonaphthofuranyl, by at least one R20Substituted or unsubstituted benzonaphthothienyl by at least one R20Substituted or unsubstituted benzonaphthocarbazolyl radical substituted by at least one R20Substituted or unsubstituted benzonaphthofluorenyl radical substituted by at least one R20Substituted or unsubstituted dibenzofuranyl, by at least one R20Substituted or unsubstituted carbazolyl, with at least one R20Substituted or unsubstituted fluorenyl.
Preferably, the compound B is any one of the following compounds B-1 to B-32:
Figure BDA0002735445750000151
Figure BDA0002735445750000161
Figure BDA0002735445750000171
the alkyl group in the invention can be any one of a straight chain and a branched chain, and optionally, the alkyl group includes but is not limited to methyl, ethyl, propyl, isopropyl, butyl, 2-butyl, isobutyl and tert-butyl.
The cycloalkyl group in the present invention means a substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantane and the like.
The aryl group comprises monocyclic, polycyclic and condensed ring aryl groups, and is selected from phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, phenylphenanthryl, anthryl, indenyl, triphenylene, pyrenyl, tetracenyl, perylenyl, chrysenyl, condensed tetraphenyl, fluoranthenyl or spiro-dibenzofluorenyl.
The heteroaryl group of the present invention includes monocyclic, polycyclic, fused ring-based heteroaryl groups selected from furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl.
The substituent groups are independently selected from deuterium atom, halogen, nitro, cyano, or unsubstituted C1-C4 alkyl, C6-C12 aryl, C3-C12 heteroaryl, or C1-C4 alkyl, C6-C12 aryl or C3-C12 heteroaryl substituted by at least one of deuterium atom, halogen, cyano or nitro, and the substituent groups can independently exist or be connected with two adjacent substituents to form a ring.
The adjacent groups are linked to form a ring, meaning that 2 substituents (e.g. R) are located at adjacent positions in the same ring1And R2，R2And R3) The adjacent 2-4 connecting rings can be connected through chemical bonds to form a ring, 2 substituents which are positioned on different rings and have a distance of 1-3 (such as 1, 2 or 3) connecting sites can be connected through chemical bonds to form a ring, and the specific ring forming mode is not limited in the invention.
In the present invention, the halogen includes fluorine, chlorine, bromine or iodine.
When reference is made herein to "substituted or unsubstituted" and no specific substituents are specified, the substituents have the same selection ranges as described above.
In the present invention, said substituted or unsubstituted C1-C10Is substituted or unsubstituted C1, C2, C3, C4, C5, C6, C7, C8, C9 or C10 alkyl; said substituted or unsubstituted C2-C10Is substituted or unsubstituted C2, C3, C4, C5, C6, C7, C8, C9 or C10 alkenyl; said substituted or unsubstituted C6-C60The aryl group of (a) is a substituted or unsubstituted aryl group of C6, C7, C8, C10, C12, C15, C18, C20, C25, C28, C30, C33, C35, C40, C45, C50, C55, C60; said substituted or unsubstituted C3-C30The heteroaryl group of (a) is a substituted or unsubstituted C3, C4, C5, C6, C7, C8, C9 or C10 heteroaryl group, and the like for other similarly defined groups.
Preferably, in the organic electroluminescent composition, the weight ratio of the compound a to the compound B is 1:99 to 99:1, such as 1:99, 1:80, 1:73, 1:65, 1:50, 1:40, 1:25, 1:15, 1:10, 1:1, 3:1, 8:1, 10:1, 20:1, 40:1, 60:1, 80:1, 90:1 or 99: 1.
In another aspect, the present invention provides an organic electroluminescent device comprising a first electrode, a second electrode and an organic layer between the first electrode and the second electrode, the organic layer comprising an organic electroluminescent composition as described above.
In the present invention, the organic layer includes at least one or a combination of at least two of 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, and contains at least a light emitting layer.
Preferably, the light-emitting layer includes a host material and a guest material, and the host material includes the organic electroluminescent composition as described above.
Preferably, the guest material is a phosphorescent dopant.
In the present invention, the dopant may be a red, green or blue dopant. The dopant is a material which is small in amount to cause light emission, and may be generally a material such as a metal complex which emits light by being excited to a triplet state or a multiple state multiple times. The dopant may be, for example, an inorganic, organic or organic/inorganic compound, and one or more of them may be used. The content of the dopant may be about 0.1 wt% to 20 wt% based on the total amount of the composition.
The dopant may be, for example, a phosphorescent dopant, and examples of the phosphorescent dopant may be organometallic compounds including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof. The remaining functional layers are commercially available materials.
In another aspect, the present invention provides an organic electroluminescent device group formed by stacking at least two organic electroluminescent devices as described above to form a series structure.
In another aspect, the present invention provides a display element including the organic electroluminescent device as described above or the group of organic electroluminescent devices as described above.
In another aspect, the present invention provides a lighting element comprising an organic electroluminescent device as described above or a group of organic electroluminescent devices as described above.
Compared with the prior art, the invention has the following beneficial effects:
the compound A has a condensed ring structure formed by four rings shown in the formula I, the mother nucleus has good electron mobility, the N-containing heterocyclic substituent is introduced at the specific position of the mother nucleus, the electron mobility in the direction of the diffusion effect of LUMO electron cloud can be increased, the stability of the compound can be increased, and the faster electron transfer characteristic is shown at the same time, and the compound A is matched with the compound B with the evaporation temperature difference within 20 ℃, so that when the compound A is applied to an organic electroluminescent device, the low driving voltage and the high efficiency can be realized.
Drawings
Fig. 1 is a schematic structural diagram of an organic electroluminescent device of the present invention, in which 1 is a substrate, 2 is an anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is a light emitting layer, 6 is an electron transport layer, 7 is an electron injection layer, and 8 is a cathode.
Detailed Description
The technical solution of the present invention is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
Synthesis example 1
Figure BDA0002735445750000191
Synthesis of intermediate 1-A-8: to a 100 ml three-necked flask, raw material 1(0.01mol), raw material 2(0.01mol) and acetic acid (50 ml) were added, and the mixture was refluxed with stirring for 8 hours, quenched with water after completion of the reaction, extracted with ethyl acetate, the organic layer was dried over anhydrous magnesium sulfate, and after removal of the organic solvent, the crude product was separated by column chromatography (ethyl acetate/hexane, 1/10 (volume ratio)) to obtain intermediate 1-A-8 (yield 48%).
Synthesis of intermediate 2-A-8: a100 ml three-necked flask was charged with intermediate 1-A-8(0.01mol), bisphenopinacolylboron (0.015mol), potassium acetate (0.2mol), (1, 1' -bis (diphenylphosphino) ferrocene) dichloropalladium (II) (5mmol), 1, 4-dioxane (40ml) and reacted at 120 ℃ for 8 hours. After completion of the reaction, it was cooled to room temperature, quenched with water, extracted with dichloromethane, the extract was dried over anhydrous magnesium sulfate, dried by spinning, and the crude product was isolated by silica gel column chromatography (ethyl acetate/hexane, 1/10 (vol.)) to obtain intermediate 2-A-8 (yield 85%).
Synthesis of A-8: taking a 100 ml double-neck round-bottom bottle, adding the intermediate 2-A-8(0.01mol), the raw material 3(0.01mol) and K respectively2CO3(0.015mol), ethanol (5 ml), water (5 ml), toluene (40ml), tetrakis (triphenylphosphine) palladium (5mmol), and the mixture was refluxed for 12 hours. After the reaction, it was cooled to room temperature. Adding water into a reaction system, extracting by dichloromethane, and sequentially adding magnesium sulfate into the obtained extract liquor for drying, filtering and spin-drying; the crude product was purified by chromatography (ethyl acetate/hexane, 1/10) to give A-8 (88% yield).
Element classificationAnd (3) analysis: c46H31N5Theoretical value: c, 84.51; h, 4.78; n, 10.71; measured value: c, 84.56; h, 4.76; n, 10.68; HRMS (ESI) M/z (M +): theoretical value: 653.2579, respectively; measured value: 653.2572.
Figure BDA0002735445750000201
synthesis of A-30: the same synthesis as A-8, except that starting material 3 was replaced with starting material 13 gave A-30 (89% yield).
Elemental analysis: c38H24N4Theoretical value: c, 85.05; h, 4.51; n, 10.44; measured value: c, 85.10; h, 4.50; n, 10.40; HRMS (ESI) M/z (M +): theoretical value: 536.2001, respectively; measured value: 536.2010.
synthesis example 2
Figure BDA0002735445750000211
Synthesis of intermediate 1-A' -2: in a 100 ml three-necked flask, a starting material 4(0.01mol), a starting material 5(0.01mol), copper trifluoromethanesulfonate (5mmol), tetrachloroethane (40ml) were added under nitrogen protection, and the mixture was reacted at 100 ℃ for 5 hours, after completion of the reaction, water was added to quench, ethyl acetate was extracted, the organic layer was dried over anhydrous magnesium sulfate, the solvent was removed by filtration, and the crude product was purified by chromatography (ethyl acetate/hexane, 1/10) to obtain an intermediate 1-a' -2 (yield 51%).
Synthesis of intermediate 2-A' -2: the difference from the synthesis method of the intermediate 2-A-8 lies in that the intermediate 1-A-8 is replaced by the intermediate 1-A '-2 (0.01mol) to obtain the intermediate 2-A' -2 (the yield is 87%)
Synthesis of A' -2: the difference from the synthesis method of A-8 is that the intermediate 2-A '-2 (0.01mol) is used for replacing the intermediate 2-A-8, and the raw material 6(0.01mol) is used for replacing the raw material 3, thus obtaining A' -2 (the yield is 89%)
Elemental analysis: c44H28N4Theoretical value: c, 86.25; h, 4.61; n, 9.14; measured value: c, 86.28; h, 4.62; n, 9.10; HRMS (ESI) M/z (M +):theoretical value: 612.2314, respectively; measured value: 612.2321.
Figure BDA0002735445750000212
synthesis of A' -61: the same as the synthesis of A '-2, except that starting material 6 was replaced with starting material 14, gave A' -61 (91% yield).
Elemental analysis: c37H23N3Theoretical value: c, 87.20; h, 4.55; n, 8.25; measured value: c, 87.15; h, 4.57; n, 8.28; HRMS (ESI) M/z (M +): theoretical value: 509.1892, respectively; measured value: 509.1897.
synthesis example 3
Figure BDA0002735445750000221
Synthesis of intermediate 1-A' -5: the difference of the synthetic method of the intermediate 2-A-8 is that the intermediate 1-A-8 is replaced by the raw material 7(0.01mol) to obtain the intermediate 1-A' -5 (the yield is 84%)
Synthesis of A' -5: the difference from the synthesis method of A-8 is that the intermediate 1-A '-5 (0.01mol) is used for replacing the intermediate 2-A-8, and the raw material 8(0.01mol) is used for replacing the raw material 3, thus obtaining A' -5 (the yield is 82%)
Elemental analysis: c40H27N3Theoretical value of S: c, 82.59; h, 4.68; n, 7.22; s, 5.51; measured value: c, 82.64; h, 4.67; n, 7.20; s, 5.49; HRMS (ESI) M/z (M +): theoretical value: 581.1926, respectively; measured value: 581.1933.
synthesis example 4
Figure BDA0002735445750000222
Synthesis of intermediate 1-A' -11: the difference from the synthesis method of the intermediate 2-A-8 lies in that the intermediate 1-A-8 is replaced by the raw material 9(0.01mol) to obtain the intermediate 1-A' -11 (the yield is 84%)
Synthesis of A' -11: the difference from the synthesis method of A-8 is that the intermediate 1-A '-11 (0.01mol) is used for replacing the intermediate 2-A-8, and the raw material 10(0.01mol) is used for replacing the raw material 3, so that A' -11 (the yield is 82%)
Elemental analysis: c47H35N3Theoretical value: c, 87.96; h, 5.50; n, 6.55; measured value: c, 88.00; h, 5.48; n, 6.52; HRMS (ESI) M/z (M +): theoretical value: 641.2831, respectively; measured value: 641.2833.
synthesis example 5
Figure BDA0002735445750000231
Synthesis of intermediate 1-A' -8: the difference of the synthetic method of the intermediate 2-A-8 is that the intermediate 1-A-8 is replaced by the raw material 11(0.01mol) to obtain the intermediate 1-A' -8 (the yield is 84%)
Synthesis of A' -8: the difference from the synthesis method of A-8 is that the intermediate 1-A '-8 (0.01mol) is used for replacing the intermediate 2-A-8, and the raw material 12(0.01mol) is used for replacing the raw material 3, so that A' -8 (the yield is 82%)
Elemental analysis: c43H28N4Theoretical value: c, 85.97; h, 4.70; n, 9.33; measured value: c, 85.93; h, 4.72; n, 9.35; HRMS (ESI) M/z (M +): theoretical value: 600.2314, respectively; measured value: 600.2321.
device embodiments and comparative examples
The organic electroluminescent devices provided in examples and comparative examples have a structure as shown in fig. 1, and include, in order from bottom to top, an anode layer 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 5, an electron transport layer 6, an electron injection layer 7, and a cathode 8, which are disposed on a substrate 1.
Wherein, the anode layer in the organic electroluminescent device is made of ITO material;
the hole injection layer material is formed by doping a compound HI-2 and a compound W (N4, N4 ' -diphenyl-N4, N4 ' -bis (9-phenyl-9H-carbazole-3-yl) biphenyl-4, 4 ' -diamine) with the following structures: wherein the mass ratio of HI-2 to compound W is 3: 97;
Figure BDA0002735445750000232
the hole transport layer material is selected from a compound NPB with the structure as follows:
Figure BDA0002735445750000241
the light-emitting layer is formed by co-doping a host material and a guest material, wherein the host material is selected from the organic electroluminescent composition (comprising a compound A and a compound B, specifically shown in Table 1) or a comparative compound, the guest material is selected from a compound RD-1, and the doping mass ratio of the host material A, the host material B and the guest material is 48:48: 4; wherein the chemical structure of the compound RD-1 is shown as follows:
Figure BDA0002735445750000242
the electron transport layer material is formed by doping compound ET-2 and compound LiQ with the following structures: wherein the mass ratio of ET-2 to LiQ doping is 1: 1;
Figure BDA0002735445750000243
the electron injection layer material is selected from a compound LiQ with the following structure:
Figure BDA0002735445750000244
the cathode layer material is a mixed material of metal Mg and Ag, wherein the mass ratio of the metal Mg to the Ag is 9: 1.
Comparative example compound:
Figure BDA0002735445750000251
the preparation of the organic electroluminescent device comprises the following steps:
1) substrate cleaning:
carrying out ultrasonic treatment on the glass substrate coated with the ITO transparent electrode in an aqueous cleaning agent (the components and concentration of the aqueous cleaning agent are that ethylene glycol solvent is less than or equal to 10wt percent and triethanolamine is less than or equal to 1wt percent), washing in deionized water, and carrying out ultrasonic treatment in a water-based solvent system under the conditions of acetone: ultrasonically removing oil in an ethanol mixed solvent (volume ratio is 1: 1), baking in a clean environment until water is completely removed, and then cleaning by using ultraviolet light and ozone;
2) evaporation:
placing the glass substrate with the anode layer in a vacuum chamber, and vacuumizing to 1 × 10-6To 2X 10-4Pa, performing vacuum evaporation on the anode layer film to form a hole injection layer material in a co-evaporation mode, wherein the HI-2 and the compound W are regulated in speed according to the mass ratio, the total evaporation speed is 0.1nm/s, and the evaporation thickness is 10 nm;
3) evaporating a hole transport layer on the hole injection layer at the evaporation rate of 0.1nm/s and the evaporation film thickness of 80 nm;
4) evaporating a luminescent layer on the hole transport layer, and evaporating a luminescent host material and an object material in vacuum in a co-evaporation mode, wherein the evaporation rate of the host material and the object material is adjusted according to the mass ratio, the total evaporation rate is 0.1nm/s, and the total evaporation film thickness is 40 nm;
5) vacuum evaporating an electron transport layer on the light emitting layer, and adjusting the evaporation rate according to the mass ratio of the compound ET-2 to LiQ, wherein the total evaporation rate is 0.1nm/s, and the total evaporation film thickness is 30 nm;
6) vacuum evaporating an electron injection layer on the electron transport layer, wherein the evaporation rate is 0.05nm/s, and the total film thickness is 1 nm;
7) and (3) evaporating a cathode layer on the electron injection layer, and adjusting the evaporation rate according to the mass ratio of the metal Mg to the metal Ag, wherein the total evaporation rate is 0.1nm/s, and the total evaporation film thickness is 80 nm.
The instrument comprises the following steps: the characteristics of the device such as current, voltage, brightness, luminescence spectrum and the like are synchronously tested by adopting a PR 650 spectrum scanning luminance meter and a Keithley K2400 digital source meter system;
and (3) testing conditions are as follows: the current density is 10mA/cm2Room temperature.
And (3) life test: the time (in hours) was recorded when the device brightness dropped to 98% of the original brightness.
The organic electroluminescent devices provided in device examples 1 to 10 and comparative examples 1 to 3 were tested, and the results are shown in table 1:
table 1 device performance test results
Figure BDA0002735445750000261
As can be seen from table 3, the organic electroluminescent composition of the present invention, when used as the host material of the light-emitting layer of the device, can reduce the driving voltage, improve the current efficiency, and prolong the service life of the device; the carrier mobility is adjusted by controlling the collocation and combination proportion of the compound A and the compound B, and the balanced carrier mobility can improve the recombination probability of carriers in a luminescent layer, thereby improving the current efficiency and prolonging the service life.
The applicant states that the present invention is illustrated by the above examples of the organic electroluminescent composition and the application thereof, but the present invention is not limited to the above examples, i.e. it does not mean that the present invention must be implemented by relying on the above examples. It will be apparent to those skilled in the art that any modification of the present invention, equivalent substitutions of selected materials and additions of auxiliary components, selection of specific modes and the like, which are within the scope and disclosure of the present invention, are contemplated by the present invention.

Claims (10)

1. An organic electroluminescent composition, characterized in that the organic electroluminescent composition comprises a compound A and a compound B, the temperature difference of the thermal decomposition temperatures of the compound A and the compound B is within 20 ℃, and the compound A has a structure shown as the following formula I:
Figure FDA0002735445740000011
wherein, Y1And Y2Each independently selected from the group consisting of single bond, N, CR11The oxygen, the oxygen or the sulfur is selected from the group consisting of O and S,
R1-R9、R11each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10Alkyl, substituted or unsubstituted C1-C10Cycloalkyl, substituted or unsubstituted C2-C10Alkenyl of, substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C3-C30Heteroaryl of (3), LOR12、LSR12、LNR13R14Or LSiR15R16R17，
R1-R9、R11Each independently exists or 2-4 adjacent groups are connected into a ring X through chemical bonds,
R12-R17each independently selected from hydrogen, substituted or unsubstituted C1-C10Alkyl, substituted or unsubstituted C1-C10Cycloalkyl, substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C3-C30Heteroaryl of (a), a plurality of R12The radicals being identical or different, R13And R14Are not connected or connected to form a ring C,
L、L1each independently selected from a single bond, substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C3-C30The heteroaryl group of (a) is a group,
ar is selected from substituted or unsubstituted C6-C60Aryl, substituted or unsubstituted C3-C60The heteroaryl group of (a) is a group,
n is an integer of 1 to 2;
the substituents are each independently selected from halogen, cyano, nitro, substituted with at least one R20Substituted or unsubstituted groups as follows: one of C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkenyl, C6-C30 aryl, C6-C30 aryloxy, C6-C30 thioaryloxy, C6-C30 arylamine, C3-C30 heteroaryl, C3-C30 heteroarylamine, or a combination of these systems;
R20selected from deuterium, cyano,Nitro, halogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, methoxy, ethoxy, propoxy, phenyl, biphenyl, naphthyl, anthryl or phenanthryl.
2. The organic electroluminescent composition according to claim 1, wherein the compound a has the structure shown in formula II below:
Figure FDA0002735445740000021
wherein, X1-X5Each independently selected from N or CR10And at least one is N;
R10selected from hydrogen, deuterium, halogen, cyano, substituted by at least one R20Substituted with the following groups: C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkenyl, C6-C30 aryl, C6-C30 aryloxy, C6-C30 thioaryloxy, C6-C30 arylamine, C3-C30 heteroaryl, C3-C30 heteroarylamine or their combination,
adjacent R10Are not connected or connected into a ring W;
Y1、Y2、R1-R9、L1is as defined in formula I;
preferably, X1-X52-3 of them are N;
preferably, ring W is substituted by at least one R20Substituted or unsubstituted groups as follows: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, benzothiophene ring, benzofuran ring, indene ring, indole ring;
further preferably, the compound A is any one of the following compounds II-1 to II-3:
Figure FDA0002735445740000031
wherein, Y1、Y2、R1-R9、L1Is as defined in formula I, R10Is as defined in formula II,
Figure FDA0002735445740000032
indicates that two adjacent R10 are connected into a ring;
preferably, Y1Is N, Y2Is CR11；
Preferably, Y2Is N, Y1Is CR11；
Preferably, Y1And Y2Are all N;
preferably, said Y is1And Y2At least one is a single bond;
preferably, said Y is1Is O, Y2Is a single bond, or Y2Is O, Y1Is a single bond;
preferably, said Y is1Is S, Y2Is a single bond, or Y2Is S, Y1Is a single bond;
preferably, said Y is1Is N, Y2Is a single bond, or Y2Is N, Y1Is a single bond;
preferably, said Y is1Is CR11，Y2Is a single bond, or Y2Is CR11，Y1Is a single bond.
3. The organic electroluminescent composition according to claim 1 or 2, wherein the compound a is any one of the following compounds a-1 to a-64, a '-1 to a' -64, and a "-1 to a" -24:
Figure FDA0002735445740000041
Figure FDA0002735445740000051
Figure FDA0002735445740000061
Figure FDA0002735445740000071
Figure FDA0002735445740000081
Figure FDA0002735445740000091
Figure FDA0002735445740000101
Figure FDA0002735445740000111
Figure FDA0002735445740000121
4. the organic electroluminescent composition according to any one of claims 1 to 3, wherein the compound B is a carbazole-based compound;
preferably, the compound B has the structure shown in formula III below:
Figure FDA0002735445740000122
wherein L is2-L4Each independently selected from a single bond, by at least one R20Substituted or unsubstituted C6-C30Aryl of (a) by at least one R20Substituted or unsubstituted C3-C30The heteroaryl group of (a);
Ar3selected from the group consisting of20Substituted or unsubstituted C6-C30Aryl of (a) by at least one R20Substituted or unsubstituted C3-C30Heteroaryl of (2), NR13R14，
m is an integer of 1-2, m1 is an integer of 0-4, m2 is an integer of 0-4, n1 is an integer of 1-2, n2 is an integer of 1-2; l is3Is a single bond, n1 is 1; l is4Is a single bond, n2 is 1;
R18-R19each independently selected from deuterium, halogen, cyano, substituted with at least one R20Substituted or unsubstituted C1-C10By at least one R20Substituted or unsubstituted C1-C10By at least one R20Substituted or unsubstituted C2-C10By at least one R20Substituted or unsubstituted C6-C30Aryl of (a) by at least one R20Substituted or unsubstituted C3-C30Heteroaryl of (A), OR12、SR12、NR13R14；
n1 Xm 1R18Identical or different, n2 Xm 2R19The same or different;
when m1 is 2 or more, R18Independently exist or are adjacent to each other to form a ring;
when m2 is 2 or more, R19Independently exist or are adjacent to each other to form a ring;
preferably, the compound B has the structure shown in formula IV below:
Figure FDA0002735445740000131
wherein L is2-L4、R18-R19、Ar3M, m2, n1 and n2 are as defined in formula III, Z1Selected from O, S, NL5Ar5、CR21R22；
Ar5Selected from the group consisting of20Substituted or unsubstituted C6-C30Aryl of (a) by at least one R20Substituted or unsubstituted C3-C30Heteroaryl of (2), NR13R14，
L5Selected from single bonds, by at least one R20Substituted or unsubstituted C6-C30Aryl of (a) by at least one R20Substituted or unsubstituted C3-C30The heteroaryl group of (a) is a group,
R21、R22each independently hydrogen, by at least one R20Substituted or unsubstituted C1-C10By at least one R20Substituted or unsubstituted C1-C10By at least one R20Substituted or unsubstituted C6-C30Aryl of (a) by at least one R20Substituted or unsubstituted C3-C30The heteroaryl group of (a);
R21、R22exist alone or are linked to form a spiro ring;
m3 is an integer from 0 to 4, n3 is an integer from 1 to 2, and m1 is an integer from 0 to 2;
preferably, the compound B has the structure shown in formula V below:
Figure FDA0002735445740000141
wherein L is2-L4、R18-R19、Ar3M, m1, m2, m3, n1, n2 and n3 are as defined in formula IV;
Z2selected from O, S, NL5Ar5、CR21R22；
Ar5Selected from the group consisting of20Substituted or unsubstituted C6-C30Aryl of (a) by at least one R20Substituted or unsubstituted C3-C30Heteroaryl of (2), NR13R14，
L5Selected from single bonds, by at least one R20Substituted or unsubstituted C6-C30Aryl of (a) by at least one R20Substituted or unsubstituted C3-C30The heteroaryl group of (a) is a group,
R21、R22each hydrogen, by at least one R20Substituted or unsubstituted C1-C10By at least one R20Substituted or unsubstituted C1-C10By at least one R20Substituted or unsubstituted C6-C30Aryl of (a) by at least one R20Substituted or unsubstituted C3-C30The heteroaryl group of (a);
R21、R22exist alone or are linked to form a spiro ring;
preferably, Ar3、Ar5Each independently selected from the group consisting of20Substituted or unsubstituted phenyl, substituted or unsubstituted by at least one R20Substituted or unsubstituted biphenyl, substituted or unsubstituted biphenyl with at least one R20Substituted or unsubstituted terphenyl group substituted by at least one R20Substituted or unsubstituted naphthyl, substituted by at least one R20Substituted or unsubstituted anthracenyl, by at least one R20Substituted or unsubstituted triphenylene, substituted or unsubstituted with at least one R20Substituted or unsubstituted pyridyl, substituted or unsubstituted with at least one R20Substituted or unsubstituted dibenzothienyl by at least one R20Substituted or unsubstituted dibenzofuranyl, by at least one R20Substituted or unsubstituted carbazolyl, with at least one R20Substituted or unsubstituted fluorenyl, NR13R14Or a combination thereof,
R13、R14each independently selected from the group consisting of20Substituted or unsubstituted phenyl, substituted or unsubstituted by at least one R20Substituted or unsubstituted biphenyl, substituted or unsubstituted biphenyl with at least one R20Substituted or unsubstituted terphenyl group substituted by at least one R20Substituted or unsubstituted naphthyl, substituted by at least one R20Substituted or unsubstituted anthracenyl, by at least one R20Substituted or unsubstitutedTriphenylene radical, substituted by at least one R20Substituted or unsubstituted pyridyl, substituted or unsubstituted with at least one R20Substituted or unsubstituted dibenzothienyl by at least one R20Substituted or unsubstituted benzonaphthofuranyl, by at least one R20Substituted or unsubstituted benzonaphthothienyl by at least one R20Substituted or unsubstituted benzonaphthocarbazolyl radical substituted by at least one R20Substituted or unsubstituted benzonaphthofluorenyl radical substituted by at least one R20Substituted or unsubstituted dibenzofuranyl, by at least one R20Substituted or unsubstituted carbazolyl, with at least one R20Substituted or unsubstituted fluorenyl.
5. The organic electroluminescent composition according to any one of claims 1 to 4, wherein the compound B is any one of the following compounds B-1 to B-32:
Figure FDA0002735445740000151
Figure FDA0002735445740000161
Figure FDA0002735445740000171
6. the organic electroluminescent composition according to any one of claims 1 to 5, wherein the weight ratio of compound A to compound B in the organic electroluminescent composition is from 1:99 to 99: 1.
7. An organic electroluminescent device comprising a first electrode, a second electrode and an organic layer between the first electrode and the second electrode, the organic layer comprising the organic electroluminescent composition according to any one of claims 1 to 6;
preferably, the organic layer comprises at least one or a combination of at least two of 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, and at least comprises a light emitting layer;
preferably, the light-emitting layer comprises a host material and a guest material, the host material comprising the organic electroluminescent composition according to any one of claims 1 to 6;
preferably, the guest material is a phosphorescent dopant.
8. An organic electroluminescent device set, wherein the organic electroluminescent device set is formed by stacking at least two organic electroluminescent devices as claimed in claim 7 in a series configuration.
9. A display element characterized in that the display element includes the organic electroluminescent device according to claim 7 or the organic electroluminescent device group according to claim 8.
10. A lighting element characterized in that the lighting element comprises the organic electroluminescent device according to claim 7 or the group of organic electroluminescent devices according to claim 8.
CN202011131958.6A 2020-10-21 2020-10-21 Organic electroluminescent composition and application thereof Active CN112358868B (en)

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CN107522665A (en) * 2016-06-20 2017-12-29 三星显示有限公司 Fused ring compound and the organic light emitting apparatus for including the fused ring compound
CN107619391A (en) * 2016-07-13 2018-01-23 三星显示有限公司 Heterocyclic compound and the organic luminescent device including the heterocyclic compound
KR20200077371A (en) * 2018-12-20 2020-06-30 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107522665A (en) * 2016-06-20 2017-12-29 三星显示有限公司 Fused ring compound and the organic light emitting apparatus for including the fused ring compound
CN107619391A (en) * 2016-07-13 2018-01-23 三星显示有限公司 Heterocyclic compound and the organic luminescent device including the heterocyclic compound
KR20200077371A (en) * 2018-12-20 2020-06-30 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof

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