CN116368109A - Carbazole and carbazole derivative-containing compound and organic electroluminescent device - Google Patents
Carbazole and carbazole derivative-containing compound and organic electroluminescent device Download PDFInfo
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- CN116368109A CN116368109A CN202280006485.8A CN202280006485A CN116368109A CN 116368109 A CN116368109 A CN 116368109A CN 202280006485 A CN202280006485 A CN 202280006485A CN 116368109 A CN116368109 A CN 116368109A
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- deuterium
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 42
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 150000001716 carbazoles Chemical class 0.000 title claims abstract description 9
- 239000010410 layer Substances 0.000 claims description 69
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 47
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 43
- 229910052805 deuterium Inorganic materials 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 29
- 125000001424 substituent group Chemical group 0.000 claims description 26
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 238000002347 injection Methods 0.000 claims description 16
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- 125000001624 naphthyl group Chemical group 0.000 claims description 13
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- 229940125904 compound 1 Drugs 0.000 description 9
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- SPDPTFAJSFKAMT-UHFFFAOYSA-N 1-n-[4-[4-(n-[4-(3-methyl-n-(3-methylphenyl)anilino)phenyl]anilino)phenyl]phenyl]-4-n,4-n-bis(3-methylphenyl)-1-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 SPDPTFAJSFKAMT-UHFFFAOYSA-N 0.000 description 1
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- 241000720974 Protium Species 0.000 description 1
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- 125000001931 aliphatic group Chemical group 0.000 description 1
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- 230000004888 barrier function Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical group [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
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- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
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- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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Abstract
The invention discloses a compound containing carbazole and carbazole derivatives and an organic electroluminescent device, and relates to the technical field of organic electroluminescent, wherein the structural formula of the compound is shown as the following formula 1. The compound is applied to an organic electroluminescent device, the luminous efficiency of the device is greatly improved under the same current density, the starting voltage is reduced, the power consumption is relatively reduced, and the service life is correspondingly prolonged.
Description
The invention relates to the technical field of organic electroluminescence, in particular to a compound containing carbazole and carbazole derivatives and an organic electroluminescent device.
An Organic Light-emitting device (OLED) is an spontaneous Light-emitting device using the following principle: when an electric field is applied, the fluorescent substance emits light by recombination of holes injected from the positive electrode and electrons injected from the negative electrode. The self-luminous device has the characteristics of low voltage, high brightness, wide viewing angle, quick response, good temperature adaptability and the like, is ultrathin, can be manufactured on a flexible panel and the like, and is widely applied to the fields of mobile phones, tablet computers, televisions, illumination and the like.
The organic plastic layer of an OLED is thinner, lighter and more flexible than the crystalline layer of an LED (light emitting diode) or LCD (liquid crystal display); the OLED is brighter than the LED, and the organic layer of the OLED is much thinner than the corresponding inorganic crystal layer in the LED, so that the conductive layer and the emitting layer of the OLED can be in a multi-layer structure, and in addition, the LED and the LCD need glass as a support, the glass absorbs a part of light, and the OLED does not need glass.
Currently, an OLED device is formed by a substrate, a cathode, an anode, a Hole Injection Layer (HIL), an Electron Injection Layer (EIL), a Hole Transport Layer (HTL), an Electron Transport Layer (ETL), an Electron Blocking Layer (EBL), a Hole Blocking Layer (HBL), an emission layer (EML), and the like, and when a voltage is applied to both electrodes of the OLED device, positive and negative charges are generated in an organic layer functional material film layer by an electric field, and the positive and negative charges are further recombined in the emission layer, so that light can be generated.
The visual field of the OLED is wide, which can reach about 170 degrees, and the LCD blocks light during operation, so that natural observation barriers exist at certain angles, and the OLED can emit light, so that the visual field is also wide.
In view of the actual demands of the current organic electroluminescent industry, the development of the current organic electroluminescent materials is far insufficient, and far falls behind the requirements of panel manufacturing enterprises.
Disclosure of Invention
The invention aims at providing a carbazole and carbazole derivative-containing compound capable of electroluminescence.
It is another object of the present invention to provide an organic electroluminescent device comprising the above compound.
The aim of the invention can be achieved by the following measures:
a compound containing carbazole and carbazole derivatives has a structural formula shown in the following formula 1:
wherein,
ra is hydrogen or deuterium;
R 1 -R 6 each independently is hydrogen, deuterium, or substituted or unsubstituted C 6-20 An aromatic group having substituents selected from deuterium, phenyl, and C 1-6 One or more of alkyl or halogen;
R 7 -R 18 each independently hydrogen, deuterium or substituted or unsubstituted phenyl, the substituents of which are selected from deuterium, C 1-6 One or more of alkyl, halogen, or phenyl;
Ar 1 is substituted or unsubstituted C 6-20 An aromatic group having substituents selected from deuterium, phenyl, and C 1-6 One or more of alkyl or halogen.
In a preferred embodiment, R 1 -R 6 Each independently is hydrogen, deuterium, or a substituted or unsubstituted group of: phenyl, biphenyl, terphenyl, anthracenyl, naphthyl, phenanthryl, fluorenyl, dibenzofuranyl or dibenzothienyl, the substituents of which are selected from deuterium, C 1-6 One or more of alkyl or phenyl.
In another preferred embodiment, R 1 -R 6 Each independently is hydrogen, deuterium, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, anthracenyl, deuterated anthracenyl, naphthyl, deuterated naphthyl, or 9, 9-dimethylfluorenyl.
In a preferred embodiment, R 7 -R 18 Each independently is hydrogen, deuterium, or a substituted or unsubstituted phenyl group, the substituents of which are selected from one or more of deuterium or phenyl.
In another preferred embodiment, R 7 -R 18 Each independently is hydrogen, deuterium, phenyl or deuterated phenyl.
In a preferred embodiment, ar 1 The following groups are substituted or unsubstituted: phenyl, biphenyl, terphenyl, anthracenyl, naphthyl, phenanthryl, fluorenyl, dibenzofuranyl or dibenzothienyl, the substituents of which are selected from deuterium, C 1-6 One or more of alkyl or phenyl.
In another preferred embodiment, ar 1 Is phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, anthracenyl, deuterated anthracenyl, naphthyl, deuterated naphthyl, phenanthryl, deuterated phenanthryl, fluorenyl, deuterated fluorenyl, dibenzofuranyl, deuterated dibenzofuranyl, dibenzothienyl, deuterated dibenzothienyl, 9-dimethylfluorenyl or deuterated 9, 9-dimethylfluorenyl.
In another preferred embodiment, ar 1 Is one of the following groups:
in another preferred embodiment, R 1 Hydrogen or deuterium.
In another preferred embodiment, R 2 Hydrogen, deuterium, phenyl or deuterated phenyl.
In another preferred embodiment, R 3 -R 6 Each independently is hydrogen or deuterium.
In another preferred embodiment, R 7 -R 10 Each independently is hydrogen or deuterium.
In another preferred embodiment, R 11 -R 14 Each independently is hydrogen or deuterium.
In another preferred embodiment, R 15 -R 18 Each independently is hydrogen, deuterium, phenyl or deuterated phenyl.
In another preferred embodiment, ar 1 Is phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, naphthyl or deuterated naphthyl.
Further, it is any one of the following compounds:
the carbazole and carbazole derivative-containing compounds represented by formula 1 of the present invention can be prepared by the following reaction schemes, wherein each group is defined as above:
the compound has excellent heat stability and can meet the use requirement of organic electroluminescent materials. In comparison with the similar compounds, the present inventionThe compound has the advantages of high luminous efficiency, low power consumption, long service life and the like. We have found that, in Ra, R 2 、R 15 -R 18 And Ar is a group 1 When a specific group is adopted, the compound has more excellent effect, the luminous efficiency of the compound can be greatly improved, the power consumption of the luminous device is lower, and the service life of the luminous device is prolonged to a greater extent.
An organic electroluminescent device comprising a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode, the organic layer containing the compound of formula 1 of the present invention.
Further, the organic layer of the organic electroluminescent device comprises a hole injection layer, a first hole transport layer, a second hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer; at least one of the hole injection layer, the first hole transport layer, the second hole transport layer, the light emitting layer, the hole blocking layer, the electron transport layer, and the electron injection layer contains the compound of formula 1 of the present invention.
Further, the compound of formula 1 of the present invention is contained in the light emitting layer of the organic electroluminescent device.
Still further, the light-emitting layer of the organic electroluminescent device further contains at least one of the following compounds G1 to G56:
the invention also provides an electronic display device which contains the organic electroluminescent device.
The invention also provides OLED lighting equipment which contains the organic electroluminescent device.
The following terms used in the claims and the specification have the following meanings unless otherwise indicated.
"Hydrogen" refers to protium (1H), which is the primary stable isotope of hydrogen.
"deuterium" refers to a stable form isotope of hydrogen, also known as deuterium, with the elemental symbol D.
"halogen" means a fluorine atom, chlorine atom, bromine atom or iodine atom.
"aromatic group", abbreviated "aryl" refers to a monocyclic, interlinked, or fused polycyclic group containing multiple carbon atoms, or further containing one or more ring heteroatoms (e.g., N, O or S), all or a portion of which have a fully conjugated pi-electron system. The number of carbon ring atoms in the aromatic group may be represented by C6-20 or the like, e.g. C 6-20 By aromatic group is meant that the number of carbon ring atoms in the aromatic group can be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, etc., up to 20. By dividing the number of carbon ring atoms, the aromatic groups being C 6-20 Aromatic group, C 6-16 Aromatic group, C 6-12 Aromatic group, C 6-10 Aromatic group, C 6-9 Aromatic group, C 6-8 Aromatic group, C 6-7 Aromatic group, C 8-16 Aromatic groups, and the like. Non-limiting examples of aromatic groups are phenyl, biphenyl, terphenyl, anthracenyl, naphthyl, phenanthryl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, 9-dimethylfluorenyl, benzimidazolyl, quinolinyl, isoquinolinyl, and the like.
"substituted or unsubstituted" means that the subsequent group may or may not have substituents. As used herein, the term "substituted" or "unsubstituted" means that at least one hydrogen in the group is re-coordinated to a hydrocarbyl group, hydrocarbon derivative group, halogen, cyano (-CN), or other substituent. The term "unsubstituted" means that all hydrogens in the group are not re-coordinated to the hydrocarbon group, hydrocarbon derivative group, halogen, cyano (-CN), or other substituents. Examples of hydrocarbyl or hydrocarbon derivative groups may include, but are not limited to, C1 to C20 alkyl, C2 to C20 alkenyl, C2 to C20 alkynyl, C6 to C20 aryl, C5 to C20 heteroaryl, C1 to C20 alkylamino, C6 to C20 arylamino, C6 to C20 heteroarylamino, C6 to C20 arylheteroarylamino, and the like.
"substituent(s) is selected from one or more of … …" means that there may be one substituent or two or more substituents in the group. When there are a plurality of substituents, there may be a plurality of the same substituents or a plurality of different substituents. Taking "one or more substituents selected from deuterium or phenyl" as an example, when a substituent is one, the substituent may be deuterium or phenyl; when the number of substituents is plural, the plural substituents may be deuterium, phenyl, deuterium, or phenyl.
"alkyl" refers to saturated aliphatic groups of 1 to 10 carbon atoms, including straight and branched chain groups (the numerical ranges mentioned herein, e.g., "1 to 10", refer to such groups, which in this case are alkyl groups, may contain 1 carbon atom, 2 carbon atoms, 3 carbon atoms, etc., up to and including 10 carbon atoms). The alkyl group may be C 1-6 Alkyl, C 1-5 Alkyl, C 1-4 Alkyl, C 1-3 Alkyl, C 1-2 Alkyl, C 2-3 Alkyl, C 2-4 Alkyl groups, and the like. Specific alkyl groups include, but are not limited to, methyl, ethyl, propyl, 2-propyl, n-butyl, isobutyl, tert-butyl, and the like.
By "+" in a group is meant the attachment site of the group to other groups or parent rings. When there are multiple attachment sites in a group to other groups or parent rings, unless explicitly mentioned, it is meant that the multiple attachment sites of the group are all possible. In the case of biphenyl, the attachment site to other groups or parent rings may be in the para, meta or ortho position of a benzene ring.
The invention has the beneficial effects that:
the invention designs a brand new organic electroluminescent material, which is formed by connecting and combining carbazole and carbazole derivatives, triazine and triazine derivatives, dibenzofuran and dibenzofuran derivatives in a specific mode. Wherein the 1-position of the dibenzofuran is an active position, the position is protected by using a benzene ring or a deuterated benzene ring and then is connected with a triazine group, and the dibenzofuran, the phenyl or the deuterated phenyl and the triazine form a meta-position relation. The connection relation has the following advantages:
1. the steric hindrance of the material molecules is improved, the triplet state energy level of the material molecules is further improved, and the reverse transfer of energy from the doped material to the main material is effectively avoided;
2. the torque of the material can be improved, the planeness of molecules of the material is reduced, the crystallinity is further reduced, the film forming property is improved, the stability of the device is improved, and the service life and the efficiency of the device are further improved;
3. the conjugation degree of the material is reduced, the rigidity of material molecules is reduced, the solubility of the material is further improved, and the preparation difficulty and cost of the material are reduced.
The compound forms a novel mother ring structure through a reasonable connection and combination mode among carbazole, triazine, dibenzofuran and benzene, and has the advantages of high luminous efficiency, low power consumption, long service life and the like under the cooperation of other groups.
Through device verification, the organic electroluminescent device prepared by using the compound disclosed by the invention has better luminous efficiency and service life.
Fig. 1 is a schematic structural view of an organic electroluminescent device according to the present invention;
the reference numerals in the figures represent: 1-anode, 2-hole injection layer, 3-first hole transport layer, 4-second hole transport layer, 5-light emitting layer, 6-hole blocking layer, 7-electron transport layer, 8-electron injection layer, 9-cathode.
FIG. 2 is an HPLC chart of Compound 1 prepared in example 1 of the present invention.
FIG. 3 is a DSC chart of Compound 1 prepared in example 1 of the present invention, and as can be seen from FIG. 3, the Tm value of Compound 1 is 245.00 ℃.
FIG. 4 is a TGA spectrum of the compound 1 prepared in example 1 of the present invention, and as can be seen from FIG. 4, the thermal weight loss temperature Td value is 433.06 ℃.
Fig. 5 is a life chart of the organic electroluminescent device in application example 1 and comparative example 1 of the present invention; as can be seen from fig. 5, the T97% lifetimes of the organic electroluminescent devices according to the present invention prepared in application example 1 and comparative example 1 were 601h and 434h, respectively.
Embodiments of the various aspects are further illustrated and described below. It should be understood that the description herein is not intended to limit the claims to the particular aspects described. On the contrary, the intent is to cover alternatives, modifications and equivalents as included within the spirit and scope of the disclosure as defined by the appended claims.
The specific conditions are not noted in the examples and are carried out according to conventional conditions or conditions recommended by the manufacturer. The reagents or apparatus used were conventional products commercially available without the manufacturer's attention.
Example 1:
the synthesis method of the compound 1 is as follows:
compound 1-a (1.1 eq,11.41g,370.25g/mol,30.83 mmol) and compound 1-b (1 eq,10g,356.81g/mol,28.03 mmol) were dissolved in 200mL of toluene under nitrogen, palladium acetate (0.31 g,224.51g/mol, 1.40 mmol), X-phos (0.26 g,476.72g/mol,1.40 mmol), potassium carbonate (11.62 g,138.21g/mol,84.08 mmol) were added, and the reaction was stirred overnight at 82℃with 100mL of ethanol and 50mL of water and monitored by HPLC.
After monitoring that the compound 1-b is reacted completely by HPLC, stopping the reaction, cooling the reaction liquid to room temperature, adding 60mL of water, stirring for 20min, carrying out suction filtration to obtain a filter cake, leaching the filter cake with water and ethanol for 2 times, then drying the filter cake at 80 ℃ for 6 hours under vacuum, adding the dried filter cake into a 250mL three-neck flask, adding 100mL o-dichlorobenzene, heating to 120 ℃ until the solid is completely dissolved, filtering the solution through a silica gel and an activated carbon funnel while the solution is hot to obtain a filtrate after the solution is completely dissolved, naturally cooling the filtrate to room temperature, precipitating white solid, carrying out suction filtration to obtain the filter cake, and carrying out recrystallization operation on the filter cake for two times to obtain the final target product compound 1, wherein the yield is 38.5%, ESI-MS (M/z) (M+): theoretical 564.63, observed 564.02, elemental analysis (formula C39H24N 4O): theoretical value C,82.96; h,4.28; n,9.92; o,2.83; actual measurement C,82.91; h,4.34; n,9.87; o,2.88.
The following compounds of table 1 were obtained in a similar manner:
TABLE 1
[ correction of 14.04.2022 according to rules 91 ]
The synthetic identification results of the compounds prepared above are shown in table 2 below:
TABLE 2
Material property testing:
the compounds 1, 6, 7, 12, 20, 32, 36, 40, 78, 83, 88, 90, 91, 95, 101, 121, 132, 174, 180, 182, 190, 219, 222, 230, 238, 250, 261, 272, 307, 315, 327 of the present invention were tested for the thermal weight loss temperature Td and the melting point Tm, and the test results are shown in table 3 below.
Note that: the thermal weight loss temperature Td is a temperature at which the weight loss is 5% in a nitrogen atmosphere, and is measured on a TGA N-1000 thermogravimetric analyzer with a nitrogen flow of 10mL/min, and a melting point Tm is measured by differential scanning calorimetry (DSC, new family DSC N-650) at a heating rate of 10 ℃/min.
Table 3:
project | Material | Td/℃ | Tm/℃ |
Example 01 | 1 | 433.06 | 245.00 |
Example 02 | 6 | 450.11 | 237.12 |
Example 03 | 7 | 415.29 | 258.07 |
Example 04 | 12 | 444.52 | 243.92 |
Example 05 | 20 | 452.81 | 255.88 |
Example 06 | 32 | 416.27 | 239.52 |
Example 07 | 36 | 425.45 | 261.80 |
EXAMPLE 08 | 40 | 428.17 | 257.46 |
Example 09 | 78 | 451.96 | 242.34 |
Example 10 | 83 | 447.16 | 230.65 |
Example 11 | 88 | 430.21 | 259.74 |
Example 12 | 90 | 448.52 | 256.17 |
Example 13 | 91 | 418.07 | 245.02 |
Example 14 | 95 | 445.46 | 238.14 |
Example 15 | 101 | 453.87 | 264.00 |
Example 16 | 121 | 418.54 | 236.12 |
Example 17 | 132 | 430.11 | 257.42 |
Example 18 | 174 | 450.61 | 239.11 |
Example 19 | 180 | 443.21 | 260.52 |
Example 20 | 182 | 415.63 | 240.86 |
Example 21 | 190 | 450.81 | 245.61 |
Example 22 | 219 | 435.64 | 234.19 |
Example 23 | 222 | 454.12 | 237.23 |
Example 24 | 230 | 419.23 | 263.71 |
Example 25 | 238 | 449.15 | 238.04 |
Example 26 | 250 | 437.25 | 256.42 |
Example 27 | 261 | 436.45 | 236.11 |
Example 28 | 272 | 455.82 | 265.32 |
Example 29 | 307 | 427.06 | 243.86 |
Example 30 | 315 | 430.51 | 248.32 |
Example 31 | 327 | 452.16 | 234.56 |
From the data, the compound synthesized by the invention has excellent thermal stability, which indicates that the compound conforming to the general structural formula of the invention has excellent thermal stability and can meet the use requirement of the organic electroluminescent material.
Device performance test:
application example 1:
ITO is adopted as the anode substrate material of the reflecting layer, and water, acetone and N are sequentially used 2 Carrying out surface treatment on the surface of the material by plasma;
depositing HT-1 doped with 2% NDP-9 (mass percent) at 10nm over an ITO anode substrate to form a Hole Injection Layer (HIL);
evaporating HT-1 of 100nm above a Hole Injection Layer (HIL) to form a first Hole Transport Layer (HTL);
vacuum evaporating GP above the first Hole Transport Layer (HTL) to form a second hole transport layer (GPL) with a thickness of 30 nm;
the compound 1 and the G1 designed by the invention are used as green main materials to be co-evaporated according to the mass ratio of 5:5, GD-1 is used as doping materials (GD-1 dosage is 8% of the total mass of the compound 1 and the G1) to be evaporated on a second hole transport layer (GPL) to form a luminescent layer with the thickness of 30 nm;
evaporating HB-1 on the light-emitting layer to obtain a Hole Blocking Layer (HBL) with the thickness of 20 nm;
co-evaporating ET-1 and LiQ on a Hole Blocking Layer (HBL) according to the proportion of 5:5 to obtain an Electron Transport Layer (ETL) with the thickness of 30 nm;
mixing and evaporating magnesium (Mg) and silver (Ag) above an Electron Transport Layer (ETL) in a mass ratio of 9:1 to form an Electron Injection Layer (EIL) with a thickness of 50 nm;
thereafter, silver (Ag) was evaporated over the electron injection layer to form a cathode having a thickness of 100nm, DNTPD having a thickness of 50nm was deposited on the above cathode sealing layer, and in addition, the surface of the cathode was sealed with UV hardening adhesive and a sealing film (seal cap) containing a moisture scavenger to protect the organic electroluminescent device from oxygen or moisture in the atmosphere, so that the organic electroluminescent device was fabricated.
Application examples 2 to 31
The organic electroluminescent devices of application examples 2 to 31 were fabricated by using the compounds 6, 7, 12, 20, 32, 36, 40, 78, 83, 88, 90, 91, 95, 101, 121, 132, 174, 180, 182, 190, 219, 222, 230, 238, 250, 261, 272, 307, 315, 327 as green host materials in examples 2 to 31 of the present invention, respectively, and the other portions were the same as application example 1.
Comparative examples 1 to 6:
the difference from application example 1 is that GH-1, GH-2, GH-3, GH-4, GH-5, GH-6 in CN110540536A was used as the green host material instead of the compound 1, and the other was the same as in application example 1.
The organic electroluminescent device manufactured in the above application example and the organic electroluminescent device manufactured in the comparative example were characterized in that the current density was 10mA/cm 2 The results of the measurement under the conditions of (2) are shown in Table 4.
Table 4:
as can be seen from the above Table 2, the compound of the present invention is applied to an organic electroluminescent device, and the luminous efficiency is greatly improved under the same current density, the starting voltage of the device is reduced, the power consumption of the device is relatively reduced, and the service life of the device is correspondingly improved.
The organic electroluminescent devices prepared in comparative examples 1 to 6 and application examples 1 to 10 were subjected to luminescence lifetime test, respectively, to obtain luminescence lifetime T97% data (time for which luminescence luminance was reduced to 97% of initial luminance), and the test equipment was a TEO luminescent device lifetime test system. The results are shown in Table 5:
table 5:
as can be seen from the above Table 5, the application of the compound of the present invention to organic electroluminescent devices has a greatly improved service life at the same current density, and has a wide application prospect.
Claims (10)
- A compound containing carbazole and carbazole derivatives is characterized in that the structural formula is shown in the following formula 1:wherein,ra is hydrogen or deuterium;R 1 -R 6 each independently is hydrogen, deuterium, or substituted or unsubstituted C 6-20 An aromatic group having substituents selected from deuterium, phenyl, and C 1-6 One or more of alkyl or halogen;R 7 -R 18 each independently hydrogen, deuterium or substituted or unsubstituted phenyl, the substituents of which are selected from deuterium, C 1-6 One or more of alkyl, halogen, or phenyl;Ar 1 is substituted or unsubstituted C 6-20 An aromatic group having substituents selected from deuterium, phenyl, and C 1-6 One or more of alkyl or halogen.
- A compound according to claim 1 wherein,R 1 -R 6 each independently is hydrogen, deuterium, or a substituted or unsubstituted group of: phenyl, biphenyl, terphenyl, anthracenyl, naphthyl, phenanthryl, fluorenyl, dibenzofuranyl or dibenzothienyl, the substituents of which are selected from deuterium, C 1-6 One or more of alkyl or phenyl;R 7 -R 18 each independently hydrogen, deuterium, or a substituted or unsubstituted phenyl group, the substituents of which are selected from one or more of deuterium or phenyl;Ar 1 the following groups are substituted or unsubstituted: phenyl, biphenyl, terphenyl, anthracenyl, naphthyl, phenanthryl, fluorenyl, dibenzofuranyl or dibenzothienyl, the substituents of which are selected from deuterium, C 1-6 One or more of alkyl or phenyl.
- a compound according to claim 1 wherein,ra is hydrogen or deuterium;R 1 hydrogen or deuterium;R 2 hydrogen, deuterium, phenyl or deuterated phenyl;R 3 -R 6 each independently hydrogen or deuterium;R 7 -R 10 each independently hydrogen or deuterium;R 11 -R 14 each independently hydrogen or deuterium;R 15 -R 18 each independently is hydrogen, deuterium, phenyl or deuterated phenyl;Ar 1 is phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, naphthyl or deuterated naphthyl.
- an organic electroluminescent device comprising a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode, wherein the organic layer comprises the compound according to any one of claims 1 to 5.
- The organic electroluminescent device of claim 6, wherein the organic layer comprises a hole injection layer, a first hole transport layer, a second hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer; at least one of the hole injection layer, the first hole transport layer, the second hole transport layer, the light emitting layer, the hole blocking layer, the electron transport layer, and the electron injection layer contains the compound according to any one of claims 1 to 5.
- an electronic display device comprising the organic electroluminescent device as claimed in claim 6.
- An OLED lighting device comprising the organic electroluminescent device as claimed in claim 6.
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