WO2022042737A1 - Composé organique pour dispositif électroluminescent organique et dispositif électroluminescent organique - Google Patents

Composé organique pour dispositif électroluminescent organique et dispositif électroluminescent organique Download PDF

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WO2022042737A1
WO2022042737A1 PCT/CN2021/115481 CN2021115481W WO2022042737A1 WO 2022042737 A1 WO2022042737 A1 WO 2022042737A1 CN 2021115481 W CN2021115481 W CN 2021115481W WO 2022042737 A1 WO2022042737 A1 WO 2022042737A1
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unsubstituted
substituted
ring
independently selected
formula
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PCT/CN2021/115481
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Chinese (zh)
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李熠烺
李国孟
李晓
曾礼昌
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北京鼎材科技有限公司
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Priority to KR1020237011222A priority Critical patent/KR20230054898A/ko
Publication of WO2022042737A1 publication Critical patent/WO2022042737A1/fr

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Definitions

  • the present invention relates to the technical field of organic light-emitting materials, in particular to an organic compound, its application and an organic electroluminescent device comprising the same.
  • OLEDs organic light emitting diodes
  • OLED organic field effect transistors
  • organic photovoltaic cells organic sensors, and the like.
  • OLED has developed rapidly and has achieved commercial success in the field of information display.
  • OLED can provide three colors of red, green and blue with high saturation.
  • the full-color display device made of OLED does not need additional backlight, and has the advantages of dazzling colors, lightness and softness.
  • the core of an OLED device is a thin film structure containing a variety of organic functional materials.
  • Common functionalized organic materials include hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, light-emitting host materials and light-emitting guests (dyes), etc. When energized, electrons and holes are injected into and transported to the light-emitting region and recombined there, thereby generating excitons and emitting light.
  • Thermally excited delayed fluorescence (TADF) technology can effectively utilize triplet excitons to achieve high luminous efficiency without using metal complexes by promoting the transition of triplet excitons to singlet excitons.
  • Thermally excited sensitized fluorescence (TASF) technology uses materials with TADF properties to sensitize the luminophore through energy transfer, which can also achieve high luminous efficiency.
  • OLED products gradually enter the market, people have higher and higher requirements for the performance of such products.
  • the currently used OLED materials and device structures cannot completely solve the problems of OLED product efficiency, lifespan, cost and other aspects. This problem is particularly prominent in deep blue light devices.
  • the object of the present invention is to provide a new class of compounds for organic electroluminescent devices.
  • the organic electroluminescent devices using such compounds can emit deep blue light, which can satisfy the requirements for OLED devices.
  • deep blue light refers to light with a wavelength of about 440 nm to 470 nm.
  • the researchers of the present invention have come up with an ingenious molecular design scheme through serious thinking and continuous experiments.
  • the compound obtained through the above scheme is very suitable for application in OLED, and the obtained device has excellent performance and can meet people's requirements.
  • one of the objects of the present invention is to provide an organic compound having the structure shown in formula (1):
  • X 1 and X 2 are each independently selected from one of CR 1 R 2 , NR 3 , O, S or SiR 4 R 5 ;
  • R 1 to R 5 When any one or more of R 1 to R 5 exists, it can optionally form a ring with Ring A or Ring D;
  • Ring A, Ring D and Ring E are each independently selected from one of substituted or unsubstituted C5-C30 aromatic rings and substituted or unsubstituted C3-C30 aromatic heterocycles, and at least one has the formula (a)
  • the structure shown in (a) is fused through ring F (to form a compound of formula (1), that is, when any one or more of ring A, ring D and ring E has the formula (a)
  • each independently is fused with the parent core structure through the ring F on the formula (a), thereby forming a compound with the structure of the formula (1));
  • Ring F and Ring G are each independently selected from substituted or unsubstituted C5-C23 aromatic rings and substituted or unsubstituted C3-C23 aromatic heterocycles;
  • Y 1 and Y 2 are each independently selected from one of CR 6 R 7 , NR 8 , O, S or SiR 9 R 10 ;
  • R 1 to R 10 are independently selected from hydrogen, halogen, cyano, nitro, hydroxyl, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 cycloalkyl
  • the substituent is selected from halogen, cyano, nitro, hydroxyl, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 One or at least two of thioalkoxy, C1-C10 silyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl and C3-C30 heteroaryl combination.
  • the compounds satisfying the structure of the general formula (1) defined in the present invention have a suitable rigid conjugated structure as the mother nucleus, and pass the methylene,
  • the imine group, O or S, etc. connect a specific aromatic group to the parent nucleus while breaking the conjugated structure between the parent nucleus and the group, so it can show high external quantum efficiency in OLED devices and Lower take-off and drop voltage.
  • the voltage and efficiency of the device can be improved, and the red shift of the light color can be avoided and the light color purity can be improved.
  • the "substituted or unsubstituted” group may be substituted with one substituent or with multiple substituents. When there are multiple substituents, they may be selected from different substituents. When the same expressions are involved in the invention, they all have the same meaning, and the selection ranges of the substituents are all as shown above and will not be repeated one by one.
  • the expressions of Ca-Cb represent that the number of carbon atoms of the group is a-b, unless otherwise specified, generally the number of carbon atoms does not include the number of carbon atoms of the substituent.
  • the expression of the ring structure crossed by "—" means that the connection site is at any position on the ring structure that can form a bond.
  • each independently means that when the subject has a plurality of them, they may be the same or different from each other.
  • the expression of chemical elements usually includes the concept of isotopes with the same chemical properties, for example, the expression of "hydrogen (H)” also includes 1 H (protium or H), The concept of 2 H (deuterium or D); carbon (C) includes 12 C, 13 C, etc., and will not be repeated here.
  • hydrogen (H) also includes 1 H (protium or H)
  • 2 H deuterium or D
  • carbon (C) includes 12 C, 13 C, etc., and will not be repeated here.
  • heteroatoms in the present invention generally refer to atoms or atomic groups selected from N, O, S, P, Si and Se, preferably selected from N, O, S.
  • the monocyclic aryl group means that the molecule contains one or at least two phenyl groups.
  • the phenyl groups are independent from each other and are connected through a single bond, exemplarily Such as phenyl, biphenyl, terphenyl, etc.
  • fused-ring aryl refers to the molecule containing at least two benzene rings, but the benzene rings are not independent of each other, but share ring edges and fused with each other, for example Such as naphthyl, anthracenyl, etc.
  • monocyclic heteroaryl group means that the molecule contains at least one heteroaryl group, when the molecule contains a heteroaryl group and other groups (such as aryl, heteroaryl, alkyl, etc.
  • the heteroaryl group and other groups are independent of each other and are connected through a single bond, such as pyridine, furan, thiophene, etc.; Condensed, or, condensed from at least two heteroaromatic rings, such as quinoline, isoquinoline, benzofuran, dibenzofuran, benzothiophene, dibenzothiophene and the like.
  • both the aryl group and the heteroaryl group include the case of a single ring and a condensed ring.
  • the substituent is not condensed with the group in which it is located.
  • the organic compound of the present invention is preferably X 1 and X 2 each independently selected from one of NR 3 , O or S. More preferably, in the organic compound of the present invention, at least one of X 1 and X 2 is NR 3 , and R 3 is one of substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups.
  • organic compound of the present invention By setting the organic compound of the present invention to have the above-mentioned structure, it is possible to have higher carrier transport performance.
  • Y 1 and Y 2 are each independently selected from one of CR 6 R 7 , NR 8 or O; more preferably, at least one of Y 1 and Y 2 is CR 6 R 7 ; further preferably, Y 1 and Y 2 is both CR 6 R 7 .
  • R 6 and R 7 are each independently selected from hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6- One of C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
  • R 6 and R 7 are each independently selected from hydrogen or one of the following groups:
  • both R6 and R7 are methyl.
  • the organic compound of the present invention By making the organic compound of the present invention the above-mentioned structure, it is possible to avoid the red shift of the light color and to improve the light color purity.
  • the organic compound of the present invention is preferably one of ring F selected from substituted or unsubstituted C5-C14 aromatic rings and substituted or unsubstituted C3-C14 aromatic heterocycles; more preferably selected from substituted or unsubstituted C5-C10 aromatic rings One of ring, substituted or unsubstituted C3-C10 N-containing aromatic heterocycles; more preferably the structure represented by formula (b):
  • * represents the condensed site with the ring in which the Y 1 Y 2 ring is located, and the ring F is condensed with the parent nucleus through Z 1 and Z 2 , Z 2 and Z 3 or Z 3 and Z 4 , and Z 1 to Z 4
  • Each is independently selected from one of C, CR 11 , and N;
  • the R 11 is each independently selected from hydrogen, halogen, cyano, nitro, hydroxyl, substituted or unsubstituted C1-C10 chain alkyl, Substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C1-C10 silyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted Or one of unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6
  • each of Z 1 to Z 4 is independently CR 11 , and each of said R 11 is independently selected from hydrogen or one of the following groups:
  • ring A, ring D and ring E are each independently selected from one of substituted or unsubstituted C5-C14 aromatic rings and substituted or unsubstituted C3-C14 aromatic heterocycles, and at least one of them has The structure shown in formula (a);
  • ring A and ring D are each independently selected from the structure represented by formula (c) or formula (a), ring E is a structure represented by formula (c') or formula (a), and ring A, ring D and at least one of ring D has the structure shown in formula (a):
  • Z 5 to Z 8 are each independently selected from one of C, CR 11 , and N;
  • the R 11 is each independently selected from hydrogen, halogen, cyano, nitro group, hydroxyl, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C1-C10 silane base, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl
  • One of the bases, R 11 is optionally connected to the adjacent aromatic ring or aromatic heterocycle to form a ring;
  • At least one of ring A and ring D is a structure represented by formula (a).
  • Z 5 to Z 8 are each independently CR 11 , and R 11 is each independently selected from hydrogen or one of the following groups:
  • ring G is selected from one of substituted or unsubstituted C5-C14 aromatic rings and substituted or unsubstituted C3-C14 aromatic heterocycles;
  • * represents the condensed site with the ring in which the Y 1 Y 2 ring is located, Z 1' to Z 4' are independently selected from one of C, CR 12 and N;
  • R 12 is independently selected from hydrogen, Halogen, cyano, nitro, hydroxyl, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted Substituted C1-C10 silyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted One of the C3-C30 heteroaryl groups, the R 12 is optionally condensed with the aromatic ring or aromatic heterocyclic ring
  • the C1-C10 alkyl group mentioned in the present invention can be, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-hexyl, n-octyl, Positive nonyl.
  • the C3-C10 cycloalkyl group mentioned in the present invention includes, for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cyclodecyl group, and the like.
  • the C1-C10 alkoxy group mentioned in the present invention includes, for example, a methoxy group, an ethoxy group, a butoxy group, a hexyloxy group, an octyloxy group, and the like.
  • the C1-C10 thioalkoxy group mentioned in the present invention includes, for example, a methylthio group, an ethylthio group, a butylthio group, a hexylthio group, an octylthio group, and the like.
  • the C1-C10 silyl group mentioned in the present invention includes, for example, a trimethylsilyl group, a triethylsilyl group, and the like.
  • the C6-C30 arylamino group mentioned in the present invention includes, for example, phenylamino, methylphenylamino, naphthylamino, anthracenylamino, phenanthrylamino, biphenylamino and the like.
  • the C3-C30 heteroarylamino group mentioned in the present invention includes, for example, a pyridylamino group, a pyrimidinylamino group, a dibenzofuranylamino group, and the like.
  • the C6-C30 aryl group mentioned in the present invention includes a C6-30 monocyclic aryl group and a C10-C30 fused-ring aryl group.
  • a C6-30 monocyclic aryl group a phenyl group, a biphenyl group, a terphenyl group, etc. are mentioned, for example.
  • the biphenyl group includes 2-biphenyl group, 3-biphenyl group and 4-biphenyl group;
  • the terphenyl group includes p-terphenyl-4-yl, p-terphenyl- 3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl.
  • C10-C30 fused-ring aryl groups include, for example, naphthyl, anthracenyl, phenanthryl, indenyl, fluorenyl, fluoranthyl, triphenylene, pyrenyl, perylene, group, naphthacyl group and their derivative groups, etc.
  • the naphthyl group includes 1-naphthyl or 2-naphthyl; the anthracenyl group is selected from 1-anthracenyl, 2-anthracenyl and 9-anthracenyl; the fluorenyl group is selected from 1-fluorenyl , 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; the pyrenyl is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the naphthacyl is selected from 1-naphthacyl, 2-naphthacyl and 9-naphthacyl.
  • the derivative group of the fluorene is selected from 9,9-dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-dipropylfluorenyl, 9,9-dibutylfluorenyl, 9,9-dibutylfluorenyl ,9-dipentylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, spirofluorenyl and benzofluorenyl.
  • the C3-C30 heteroaryl groups mentioned in the present invention include C3-C30 monocyclic heteroaryl groups and C6-C30 fused-ring heteroaryl groups.
  • the C3-C30 monocyclic heteroaryl group includes a furyl group, a thienyl group, a pyrrolyl group, and a pyridyl group.
  • C6-C30 fused ring heteroaryl groups include benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, acridine Peridyl, isobenzofuranyl, isobenzothienyl, acridinyl, pyridyl, benzocarbazolyl, azacarbazolyl, phenothiazinyl, phenazinyl and the like.
  • Specific examples of the arylene group in the present invention include divalent groups obtained by removing one hydrogen atom from the examples of the above-mentioned aryl group.
  • Specific examples of the heteroarylene group in the present invention include divalent groups obtained by removing one hydrogen atom from the above examples of the heteroaryl group.
  • the aryloxy group in the present invention includes a monovalent group consisting of the above-mentioned aryl group, heteroaryl group, and oxygen.
  • the C6-C30 arylamino group mentioned in the present invention includes, for example, phenylamino, methylphenylamino, naphthylamino, anthracenylamino, phenanthrylamino, biphenylamino and the like.
  • the C3-C30 heteroarylamino group mentioned in the present invention includes, for example, a pyridylamino group, a pyrimidinylamino group, a dibenzofuranylamino group, and the like.
  • Z 11 to Z 18 , Z 5 ′ to Z 7 ′ have the same range as Z 1 to Z 4 in the foregoing, and R 8 ′ and R 8 ′′ have the same range as R 8 in the foregoing. Scope.
  • the compound of the general formula of the present invention is preferably the following specific compounds, but the present invention is not limited to the following specific compounds:
  • an application of the above compound in an organic electroluminescent device is also provided. Specifically, it is preferably used as a light-emitting layer material in an organic electroluminescent device.
  • an organic electroluminescence device comprising a first electrode, a second electrode and an organic layer interposed between the first electrode and the second electrode, the organic layer containing Compounds of general formula (1) as described above.
  • the compound of the general formula (1) of the present invention has a suitable rigid conjugated structure as a parent nucleus, and connects a specific aromatic group to the parent nucleus through a methylene group, an imino group, O or S, etc., while interrupting the parent nucleus
  • the conjugated structure with this group can therefore show higher external quantum efficiency and lower take-off and fall voltage in OLED devices.
  • the compound obtained by linking the above specific core and the above specific aromatic group through the above specific method is used as a light emitting layer dye, the voltage and efficiency of the device can be improved, and the red shift of the light color can be avoided and the light color purity can be improved.
  • the compound obtained through the above scheme is very suitable for application in OLED, and the obtained device has excellent performance and can meet people's requirements.
  • the synthesis method is similar to that of Synthesis Example 1, except that the raw material 2 is replaced with an equivalent amount of the raw material 3 to obtain 56.6 g of the product (intermediate M2).
  • the synthesis method of P16 was similar to that of P1, and the product 19.8g (P16) was finally obtained.
  • the synthesis method was similar to that of Synthesis Example 1, except that the raw material 1 was replaced with an equivalent amount of the raw material 4 to obtain 28.2 g of the product (intermediate M3).
  • the synthesis method of P29 was similar to that of P1, and the final product 9.87g (P29) was obtained.
  • intermediate M4 15g, 31.75mmol
  • raw material 3 5.4g, 31.75mmol
  • Pd132 0.45g, 0.64mmol
  • sodium tert-butoxide 7.62g, 79.4mmol
  • Xylene 200ml
  • nitrogen was replaced three times, the temperature was raised to 120°C and the reaction was stopped for 12h, then the heating was stopped, filtered and evaporated to dryness, and purified by column chromatography (petroleum ether:dichloromethane 10:1) to obtain 16.7g of the product (intermediate M5).
  • the synthesis method was similar to that of Synthesis Example 4, except that the raw material 5 was replaced with an equivalent amount of the raw material 6 to obtain 11.3 g of the product (intermediate M6).
  • the synthesis method of P54 was similar to that of P53, and finally 4.6 g of the product (P54) was obtained.
  • Gaussian03 is used to perform quantum chemical calculation on the compound
  • time-dependent density functional method is used to perform theoretical calculation on P1, P16, P29, P53, P54, P84, P96 and C1, C2 respectively, and the calculation results are shown in Table 1.
  • the fluorescence emission wavelength of the material is related to the energy level of the first singlet state, and the higher the energy level, the shorter the fluorescence emission wavelength of the material, and the bluer the emission.
  • the phosphorescence emission wavelength of the material is related to the energy level of the first triplet state, and the higher the energy level, the shorter the phosphorescence emission wavelength of the material, and the bluer the emission.
  • the photoluminescence efficiency of the material is related to the intensity of the first singlet oscillator, and the larger the value of the first singlet oscillator intensity, the higher the luminous efficiency of the material.
  • the material of the present invention can still maintain a relatively high first singlet state energy level and first triplet state energy level after condensing a rigid aromatic ring outside the saturated six-membered ring, which is similar to the reference material C1.
  • the exciton energy level of the material C1 is the same as that of the compound of the present invention, but the intensity of the first singlet oscillator is relatively low, so its luminous efficiency may be relatively poor.
  • the material C2 is fused with an aromatic ring outside the five-membered ring, which essentially forms a large conjugated structure, and its first singlet energy level is lower than that of the compound of the present invention, so its emission wavelength may be longer, which cannot meet the deep blue light. device needs.
  • the OLED includes a first electrode and a second electrode, and an organic material layer between the electrodes.
  • the organic material can in turn be divided into multiple regions.
  • the organic material layer may include a hole transport region, a light emitting layer, and an electron transport region.
  • a substrate may be used under the first electrode or over the second electrode.
  • the substrates are glass or polymer materials with excellent mechanical strength, thermal stability, water resistance and transparency.
  • a thin film transistor (TFT) may be provided on a substrate as a display.
  • the first electrode may be formed by sputtering or depositing a material used as the first electrode on the substrate.
  • oxide transparent conductive materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO 2 ), zinc oxide (ZnO) or any combination thereof can be used.
  • ITO indium tin oxide
  • IZO indium zinc oxide
  • SnO 2 tin dioxide
  • ZnO zinc oxide
  • magnesium (Mg) silver
  • silver (Ag) aluminum
  • Al-lithium (Al-Li) aluminum-lithium (Al-Li)
  • ytterbium (Yb) magnesium-indium
  • Mg-In magnesium-silver
  • Mg-Ag magnesium-silver
  • other metals or alloys or any combination between them.
  • the organic material layer can be formed on the electrode by vacuum thermal evaporation, spin coating, printing and other methods.
  • the compound used as the organic material layer may be an organic small molecule, an organic macromolecule or a polymer, or a combination thereof.
  • the hole transport region is located between the anode and the light emitting layer.
  • the hole transport region may be a hole transport layer (HTL) with a single-layer structure, including a single-layer hole-transport layer containing only one compound and a single-layer hole-transport layer containing multiple compounds.
  • the hole transport region can also be a multilayer structure including at least one of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL); wherein the HIL is located between the anode and the HTL, and the EBL between the HTL and the light-emitting layer.
  • HIL hole injection layer
  • HTL hole transport layer
  • EBL electron blocking layer
  • the material of the hole transport region can be selected from, but not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene vinylene, polyaniline/dodecylbenzenesulfonic acid (Pani /DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly( 4-styrenesulfonate) (Pani/PSS), aromatic amine derivatives such as the compounds shown in HT-1 to HT-51 below; or any combination thereof.
  • phthalocyanine derivatives such as CuPc
  • conductive polymers or polymers containing conductive dopants such as polyphenylene vinylene, polyaniline/dodecylbenzenesulfonic acid (Pani /DBSA), poly(3,
  • the hole injection layer is located between the anode and the hole transport layer.
  • the hole injection layer may be a single compound material or a combination of multiple compounds.
  • the hole injection layer can use one or more compounds of the above-mentioned HT-1 to HT-51, or use one or more compounds of the following HI-1-HI-3;
  • HT-1 can also be used
  • the light-emitting layer includes light-emitting dyes (ie dopant, dopant) that can emit different wavelength spectra, and may also include a host material (Host).
  • the light-emitting layer may be a monochromatic light-emitting layer that emits a single color such as red, green, and blue.
  • the monochromatic light-emitting layers of a plurality of different colors can be arranged in a plane according to a pixel pattern, or can be stacked together to form a colored light-emitting layer. When light-emitting layers of different colors are stacked together, they can be spaced from each other or connected to each other.
  • the light-emitting layer may also be a single-color light-emitting layer capable of simultaneously emitting different colors such as red, green, and blue.
  • different materials such as fluorescent electroluminescent materials, phosphorescent electroluminescent materials, and thermally activated delayed fluorescent light emitting materials can be used as materials for the light emitting layer.
  • a single light-emitting technology can be used, or a combination of multiple different light-emitting technologies can be used.
  • These different luminescent materials, classified by technology, can emit light of the same color, or they can emit light of different colors.
  • the light-emitting layer adopts the technology of fluorescent electroluminescence.
  • the fluorescent host material of the light-emitting layer can be selected from, but not limited to, a combination of one or more of BFH-1 to BFH-17 listed below.
  • the light-emitting layer adopts the technology of thermally activated delayed fluorescence emission.
  • the host material of the light-emitting layer is selected from but not limited to a combination of one or more of the above-mentioned PH-1 to PH-85.
  • the light-emitting layer adopts the technology of thermally activated delayed fluorescence emission.
  • Its light-emitting layer fluorescent dopant can be selected from, but not limited to, a combination of one or more of TDE1-TDE37 listed below.
  • an electron blocking layer is located between the hole transport layer and the light emitting layer.
  • the electron blocking layer can adopt, but is not limited to, one or more compounds of the above-mentioned HT-1 to HT-51, or one or more compounds of the above-mentioned PH-47 to PH-77; Limited to mixtures of one or more compounds from HT-1 to HT-51 and one or more compounds from PH-47 to PH-77.
  • the OLED organic material layer may also include an electron transport region between the light-emitting layer and the cathode.
  • the electron transport region may be an electron transport layer (ETL) with a single-layer structure, including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing multiple compounds.
  • the electron transport region may also be a multilayer structure including at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).
  • EIL electron injection layer
  • ETL electron transport layer
  • HBL hole blocking layer
  • the electron transport layer material may be selected from, but not limited to, a combination of one or more of ET-1 to ET-65 listed below.
  • a hole blocking layer is located between the electron transport layer and the light emitting layer.
  • the hole blocking layer can adopt, but is not limited to, one or more compounds of the above-mentioned ET-1 to ET-65, or adopt, but not limited to, one or more compounds of PH-1 to PH-46; or A mixture of one or more compounds of ET-1 to ET-65 and one or more compounds of PH-1 to PH-46 is employed, but not limited to.
  • the device may also include an electron injection layer between the electron transport layer and the cathode, and the material of the electron injection layer includes but is not limited to a combination of one or more of the following: LiQ, LiF, NaCl, CsF, Li 2 O, Cs 2 CO 3 , BaO, Na, Li, Ca, Mg, Yb.
  • the glass plate coated with the ITO transparent conductive layer was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreasing in an acetone:ethanol mixed solvent, baked in a clean environment until the water was completely removed, and UV light was used. Light and ozone cleaning, and bombarding the surface with a beam of low-energy cations;
  • the above-mentioned glass substrate with anode is placed in a vacuum chamber, evacuated to ⁇ 1 ⁇ 10 -5 Pa, and 10nm of HT-4:HI-3 (97 nm) is vacuum thermally evaporated on the above-mentioned anode layer film in sequence.
  • Example 1 Except for replacing P1 in Example 1 with the corresponding compounds in Table 2, the same procedure as in Example 1 was carried out to obtain Examples 2 to 9 and Comparative Examples 1 to 2 (respectively replaced P1 with compounds C1 and C2). Organic Electroluminescent Devices.
  • the driving voltage and external quantum efficiency (EQE) of the organic electroluminescent devices prepared in Examples 1-22 and Comparative Examples 1-2 were measured using a digital source meter and a luminance meter. Specifically, the voltage was increased at a rate of 0.1V per second, the voltage when the luminance of the organic electroluminescence device reached 1000cd/m 2 , that is, the driving voltage, was measured, and the external quantum efficiency at this time was also measured.
  • the BN-based organic material of the present invention is used in organic electroluminescence devices, because of its stronger rigid structure, it also has better carrier transport properties, which is helpful for It exhibits higher external quantum efficiency and lower voltage in OLED devices.
  • the B-N organic material of the present invention has a more bluish light color when used in an organic electroluminescent device. It is presumed that this is because C2 does not have the group represented by the formula (1) in the compound of the present invention, so when it is used in an organic electroluminescent device, it emits sky blue light (470nm-490nm) and cannot obtain deep blue light.
  • the larger fused rigid ring structure of the compound of the present invention is favorable for the near-planar arrangement of molecules, which is favorable for light extraction, thereby improving its external quantum efficiency.
  • the performance of the organic electroluminescent devices of Examples 12 to 15 is better than that of Comparative Example 1, but is slightly insufficient compared to Example 1.
  • the luminescent layer dye of the organic electroluminescence device of Example 1 adopts the compound P1 of the present invention
  • X 1 and X 2 are both NR 3
  • the organic electroluminescence devices of Examples 12 to 15 adopt the compound P1 of the present invention.
  • the compounds are P181-P184, wherein X 1 and X 2 are CR 1 R 2 , O, S and SiR 4 R 5 respectively.
  • Example 12 using P184 Example 15 This may be due to the compound of the general formula (1) of the present invention obtained by connecting a specific aromatic group to the parent nucleus through an imine group while breaking the conjugated structure between the parent nucleus and the group, the first single line of the compound of the present invention is The state oscillator strength is relatively high and thus exhibits high external quantum efficiency.

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Abstract

La présente invention concerne un composé organique, son utilisation, et un dispositif électroluminescent organique comprenant le composé organique. Le composé organique a la structure telle que représentée par la formule (1). X1 et X2 sont chacun indépendamment choisis parmi CR1R2, NR3, O, S ou SiR4R5. L'un quelconque de R1-R5 forme un cycle avec le cycle A ou le cycle D. Le cycle A, le cycle D, et le cycle E sont chacun indépendamment choisis parmi un cycle aromatique en C5-C30 et un cycle hétéroaromatique en C3-C30, et au moins l'un du cycle A, du cycle D et du cycle E a la structure telle que représentée par la formule (a). La structure telle que représentée par la formule (a) est fusionnée par le cycle F. Le cycle F et le cycle G sont chacun indépendamment choisis parmi un cycle aromatique en C5-C23 et un cycle hétéroaromatique en C3-C23. Y1 et Y2 sont chacun indépendamment choisis parmi CR6R7, NR8, O, S ou SiR9R10. R1-R10 sont chacun indépendamment choisis parmi l'hydrogène, halogène, cyano, nitro, hydroxyle, alkyle à chaîne en C1-C10, cycloalkyle en C3-C10, alcoxy en C1-C10, amino, silyle en C1-C10, aryle en C6-C30 et hétéroaryle en C3-C30.
PCT/CN2021/115481 2020-08-31 2021-08-30 Composé organique pour dispositif électroluminescent organique et dispositif électroluminescent organique WO2022042737A1 (fr)

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