CN117561234A - Compounds and organic light-emitting devices containing the same - Google Patents
Compounds and organic light-emitting devices containing the same Download PDFInfo
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- CN117561234A CN117561234A CN202380012489.1A CN202380012489A CN117561234A CN 117561234 A CN117561234 A CN 117561234A CN 202380012489 A CN202380012489 A CN 202380012489A CN 117561234 A CN117561234 A CN 117561234A
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- deuterium
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- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 4
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- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 3
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- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
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- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 150000002537 isoquinolines Chemical class 0.000 description 1
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- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- ANYCDYKKVZQRMR-UHFFFAOYSA-N lithium;quinoline Chemical compound [Li].N1=CC=CC2=CC=CC=C21 ANYCDYKKVZQRMR-UHFFFAOYSA-N 0.000 description 1
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- AMTZBMRZYODPHS-UHFFFAOYSA-N manganese;quinolin-8-ol Chemical compound [Mn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 AMTZBMRZYODPHS-UHFFFAOYSA-N 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006610 n-decyloxy group Chemical group 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006609 n-nonyloxy group Chemical group 0.000 description 1
- 125000006608 n-octyloxy group Chemical group 0.000 description 1
- 125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000005484 neopentoxy group Chemical group 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- UHHKSVZZTYJVEG-UHFFFAOYSA-N oxepane Chemical compound C1CCCOCC1 UHHKSVZZTYJVEG-UHFFFAOYSA-N 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
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- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003246 quinazolines Chemical class 0.000 description 1
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- 125000005493 quinolyl group Chemical group 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 150000004905 tetrazines Chemical class 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
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- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
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- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/60—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton containing a ring other than a six-membered aromatic ring forming part of at least one of the condensed ring systems
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
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- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
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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
- C07D405/02—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 two hetero rings
- C07D405/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
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- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
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Abstract
本说明书提供由化学式1表示的化合物及包含其的有机发光器件。
This specification provides a compound represented by Chemical Formula 1 and an organic light-emitting device including the same.
Description
技术领域Technical Field
本申请主张于2022年04月12日向韩国专利局提交的韩国专利申请第10-2022-0045344号的优先权,该韩国专利申请的文献中公开的全部内容包含在本说明书中。This application claims the priority of Korean Patent Application No. 10-2022-0045344 filed with the Korean Intellectual Property Office on April 12, 2022, and all contents disclosed in the document of the Korean patent application are incorporated into this specification.
本说明书涉及化合物及包含其的有机发光器件。The present invention relates to a compound and an organic light-emitting device including the same.
背景技术Background Art
通常情况下,有机发光现象是指利用有机物质将电能转换为光能的现象。利用有机发光现象的有机发光器件通常具有包括阳极和阴极以及位于它们之间的有机物层的结构。在这里,为了提高有机发光器件的效率和稳定性,有机物层大多情况下由分别利用不同的物质构成的多层结构形成,例如,可以由空穴注入层、空穴传输层、发光层、电子传输层、电子注入层等形成。对于这样的有机发光器件的结构而言,如果在两电极之间施加电压,则空穴从阳极注入有机物层,电子从阴极注入有机物层,当所注入的空穴和电子相遇时会形成激子(exciton),该激子重新跃迁至基态时就会发出光。Generally speaking, the phenomenon of organic light emitting refers to the phenomenon of converting electrical energy into light energy using organic substances. An organic light emitting device using the phenomenon of organic light emitting generally has a structure including an anode and a cathode and an organic layer located between them. Here, in order to improve the efficiency and stability of the organic light emitting device, the organic layer is mostly formed by a multilayer structure composed of different substances, for example, it can be formed by a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. For the structure of such an organic light emitting device, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed, and when the excitons re-transition to the ground state, light is emitted.
持续要求开发用于如上所述的有机发光器件的新的材料。There is a continuous demand for the development of new materials for organic light-emitting devices as described above.
现有技术文献Prior art literature
专利文献Patent Literature
(专利文献1)KR 10-2014-0076888(Patent Document 1) KR 10-2014-0076888
发明内容Summary of the invention
技术课题Technical issues
本说明书提供化合物及包含其的有机发光器件。The present specification provides a compound and an organic light-emitting device including the same.
课题的解决方法Solution to the problem
本说明书的一实施方式提供由下述化学式1表示的化合物。One embodiment of the present specification provides a compound represented by the following Chemical Formula 1.
[化学式1][Chemical formula 1]
在上述化学式1中,In the above chemical formula 1,
R1和R2彼此相同或不同,各自独立地为氢、氘、取代或未取代的烷基、或者取代或未取代的芳基,R1 and R2 are the same as or different from each other and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl,
R1和R2中的至少一个为碳原子数1至3的烷基,At least one of R1 and R2 is an alkyl group having 1 to 3 carbon atoms,
R2中的至少一个为取代或未取代的烷基、或者取代或未取代的芳基,At least one of R2 is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group,
R3和R4彼此相同或不同,各自独立地为氢、氘、取代或未取代的烷基、或者取代或未取代的芳基,或者与相邻的基团彼此结合而形成取代或未取代的烃环基,R3 and R4 are the same or different from each other, and are independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or are combined with adjacent groups to form a substituted or unsubstituted hydrocarbon ring group,
R5为氢、氘、取代或未取代的烷基、或者取代或未取代的芳基,R5 is hydrogen, deuterium, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl,
R3和R4为取代或未取代的芳基,或者与相邻的基团彼此结合而形成取代或未取代的烃环基时,R5中的至少一个为取代或未取代的芳基,When R3 and R4 are substituted or unsubstituted aryl groups, or when they are combined with adjacent groups to form a substituted or unsubstituted hydrocarbon ring group, at least one of R5 is a substituted or unsubstituted aryl group,
Ar1为取代或未取代的芳基、或者取代或未取代的杂环基,Ar1 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
L1和L2彼此相同或不同,各自独立地为直接键合、取代或未取代的亚芳基、或者取代或未取代的2价的杂环基,L1 and L2 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group,
a为1至8的整数,a为2以上时,R1彼此相同或不同,a is an integer from 1 to 8, and when a is 2 or more, R1 are the same or different from each other,
b为1至3的整数,b为2以上时,R2彼此相同或不同,b is an integer from 1 to 3, and when b is 2 or more, R2 are the same or different from each other,
c为1至7的整数,c为2以上时,R5彼此相同或不同。c is an integer of 1 to 7, and when c is 2 or more, R5 are the same as or different from each other.
另外,本说明书的一实施方式提供一种有机发光器件,其中,包括:阳极、阴极、以及设置在上述阳极与上述阴极之间的1层以上的有机物层,上述有机物层中的1层以上包含由上述化学式1表示的化合物。In addition, one embodiment of the present specification provides an organic light-emitting device, which includes: an anode, a cathode, and one or more organic layers arranged between the anode and the cathode, and one or more of the organic layers contain the compound represented by the above Chemical Formula 1.
发明效果Effects of the Invention
本说明书中记载的化合物可以用作有机发光器件的有机物层的材料。根据本说明书的至少一个实施方式的化合物在有机发光器件中可以实现效率的提高、较低的驱动电压和/或寿命特性的提高。特别是,本说明书中记载的化合物可以用作空穴注入、空穴传输、空穴注入和空穴传输、电子阻挡、发光、空穴阻挡、电子传输、或者电子注入的材料。此外,与现有的有机发光器件相比,具有低驱动电压、高效率和/或长寿命的效果。The compounds described in this specification can be used as materials for the organic layer of an organic light-emitting device. The compounds according to at least one embodiment of this specification can achieve improved efficiency, lower driving voltage and/or improved life characteristics in an organic light-emitting device. In particular, the compounds described in this specification can be used as materials for hole injection, hole transport, hole injection and hole transport, electron blocking, luminescence, hole blocking, electron transport, or electron injection. In addition, compared with existing organic light-emitting devices, it has the effects of low driving voltage, high efficiency and/or long life.
附图说明BRIEF DESCRIPTION OF THE DRAWINGS
图1图示了依次层叠有基板1、阳极2、有机物层10和阴极9的有机发光器件的例子。FIG. 1 illustrates an example of an organic light-emitting device in which a substrate 1 , an anode 2 , an organic layer 10 , and a cathode 9 are sequentially stacked.
图2图示了依次层叠有基板1、阳极2、空穴注入层3、空穴传输层4、电子阻挡层5、发光层6、空穴阻挡层7、电子注入和传输层8、以及阴极9的有机发光器件的例子。2 illustrates an example of an organic light-emitting device having a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, a hole blocking layer 7, an electron injection and transport layer 8, and a cathode 9 stacked in sequence.
[符号说明][Explanation of symbols]
1:基板1: Substrate
2:阳极2: Anode
3:空穴注入层3: Hole injection layer
4:空穴传输层4: Hole transport layer
5:电子阻挡层5: Electron blocking layer
6:发光层6: Luminous layer
7:空穴阻挡层7: Hole blocking layer
8:电子注入和传输层8: Electron injection and transport layer
9:阴极9: Cathode
10:有机物层10: Organic layer
具体实施方式DETAILED DESCRIPTION
下面,对本说明书更详细地进行说明。Next, this specification is described in more detail.
在本说明书中,当指出某一部分“包括/包含”某一构成要素时,只要没有特别相反的记载,则意味着可以进一步包括其它构成要素,而不是将其它构成要素排除。In the present specification, when it is indicated that a certain part “includes/comprises” a certain constituent element, unless there is a particular description to the contrary, it means that other constituent elements may be further included, rather than excluding other constituent elements.
在本说明书中,当指出某一构件位于另一个构件“上”时,其不仅包括某一构件与另一构件相接的情况,还包括两构件之间存在其它构件的情况。In the present specification, when it is mentioned that a certain component is located “on” another component, it not only includes the case where the certain component is in contact with the other component, but also includes the case where other components exist between the two components.
在本说明书中,取代基的例示在下文中进行说明,但并不限定于此。In the present specification, examples of substituents are described below, but are not limited thereto.
上述“取代”这一用语是指结合在化合物的碳原子上的氢原子被替换成其它取代基,被取代的位置只要是氢原子可以被取代的位置、即取代基可以取代的位置就没有限定,当取代2个以上时,2个以上的取代基可以彼此相同或不同。The term "substituted" mentioned above means that a hydrogen atom bonded to a carbon atom of a compound is replaced by another substituent. The substituted position is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted. When there are more than two substitutions, the two or more substituents may be the same or different from each other.
在本说明书中,“取代或未取代的”这一用语是指被选自氘、卤素基团、腈基(-CN)、硝基、羟基、烷基、环烷基、烷氧基、氧化膦基、芳氧基、烷基硫基芳基硫基烷基磺酰基芳基磺酰基烯基、甲硅烷基、硼基、胺基、芳基或杂环基中的1个或2个以上的取代基取代,或者被上述例示的取代基中的2个以上的取代基连接而成的取代基取代,或者不具有任何取代基。例如,“2个以上的取代基连接而成的取代基”可以为联苯基。即,联苯基可以为芳基,也可以被解释为2个苯基连接而成的取代基。In the present specification, the term "substituted or unsubstituted" refers to a group selected from deuterium, a halogen group, a nitrile group (-CN), a nitro group, a hydroxyl group, an alkyl group, a cycloalkyl group, an alkoxy group, a phosphine oxide group, an aryloxy group, an alkylthio group, Arylthio Alkylsulfonyl Arylsulfonyl The alkylene group may be substituted with one or more substituents selected from the group consisting of alkenyl, silyl, boronyl, amine, aryl or heterocyclic groups, or may be substituted with a substituent formed by connecting two or more substituents selected from the group consisting of the above-mentioned substituents, or may not have any substituent. For example, the "substituent formed by connecting two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group, or may be interpreted as a substituent formed by connecting two phenyl groups.
在本说明书中,“取代或未取代的”这一用语是指被选自氘、卤素基团、腈基、硝基、羟基、氨基、甲硅烷基、硼基、烷氧基、芳氧基、烷基、环烷基、芳基、以及杂环基中的1个或2个以上的取代基取代,或者被上述例示的取代基中的2个以上的取代基连接而成的取代基取代,或者不具有任何取代基。In the present specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, an amino group, a silyl group, a boron group, an alkoxy group, an aryloxy group, an alkyl group, a cycloalkyl group, an aryl group, and a heterocyclic group, or substituted with a substituent formed by connecting two or more substituents among the substituents exemplified above, or having no substituent.
在本说明书中,“取代或未取代的”这一用语是指被选自氘、卤素基团、腈基、烷基、芳基、以及杂环基中的1个或2个以上的取代基取代,或者被上述例示的取代基中的2个以上的取代基连接而成的取代基取代,或者不具有任何取代基。In this specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from deuterium, a halogen group, a nitrile group, an alkyl group, an aryl group, and a heterocyclic group, or substituted with a substituent formed by connecting two or more substituents among the substituents exemplified above, or having no substituent.
上述取代基的例示在下文中进行说明,但并不限定于此。Examples of the above substituents are described below, but are not limited thereto.
在本说明书中,作为卤素基团的例子,有氟(-F)、氯(-Cl)、溴(-Br)或碘(-I)。In the present specification, as examples of the halogen group, there are fluorine (—F), chlorine (—Cl), bromine (—Br) or iodine (—I).
在本说明书中,甲硅烷基可以由-SiYaYbYc的化学式表示,上述Ya、Yb和Yc各自可以为氢、取代或未取代的烷基、或者取代或未取代的芳基。上述甲硅烷基具体有三甲基甲硅烷基、三乙基甲硅烷基、叔丁基二甲基甲硅烷基、乙烯基二甲基甲硅烷基、丙基二甲基甲硅烷基、三苯基甲硅烷基、二苯基甲硅烷基、苯基甲硅烷基等,但并不限定于此。In the present specification, the silyl group can be represented by the chemical formula -SiYaYbYc , wherein each of Ya , Yb and Yc can be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. The silyl group specifically includes trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl and the like, but is not limited thereto.
在本说明书中,硼基可以由-BYdYe的化学式表示,上述Yd和Ye各自可以为氢、取代或未取代的烷基、或者取代或未取代的芳基。上述硼基具体有三甲基硼基、三乙基硼基、叔丁基二甲基硼基、三苯基硼基、苯基硼基等,但并不限定于此。In the present specification, the boryl group can be represented by the chemical formula -BYdYe , wherein Yd and Ye can each be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. The boryl group specifically includes trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, phenylboryl, etc., but is not limited thereto.
在本说明书中,上述烷基可以为直链或支链,碳原子数没有特别限定,但优选为1至60。根据一实施方式,上述烷基的碳原子数为1至30。根据另一实施方式,上述烷基的碳原子数为1至20。根据另一实施方式,上述烷基的碳原子数为1至10。作为烷基的具体的例子,有甲基、乙基、丙基、正丙基、异丙基、丁基、正丁基、异丁基、叔丁基、戊基、正戊基、己基、正己基、庚基、正庚基、辛基、正辛基等,但并不限定于此。In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 30. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, pentyl, n-pentyl, hexyl, n-hexyl, heptyl, n-heptyl, octyl, n-octyl, etc., but are not limited thereto.
在本说明书中,芳基烷基除了被芳基取代以外,可以适用上述的关于烷基的说明。In the present specification, the above description about the alkyl group is applicable to the arylalkyl group except that the arylalkyl group is substituted with an aryl group.
在本说明书中,上述烷氧基可以为直链、支链或环状。烷氧基的碳原子数没有特别限定,但优选碳原子数为1至20。具体而言,可以为甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、叔丁氧基、仲丁氧基、正戊氧基、新戊氧基、异戊氧基、正己氧基、3,3-二甲基丁氧基、2-乙基丁氧基、正辛氧基、正壬氧基、正癸氧基等,但并不限定于此。In this specification, the alkoxy group may be straight chain, branched chain or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but preferably the number of carbon atoms is 1 to 20. Specifically, it may be a methoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group, a n-butoxy group, an isobutoxy group, a tert-butoxy group, a sec-butoxy group, a n-pentoxy group, a neopentoxy group, an isopentyl group, a n-hexyl group, a 3,3-dimethylbutoxy group, a 2-ethylbutoxy group, a n-octyloxy group, a n-nonyloxy group, a n-decyloxy group, etc., but is not limited thereto.
本说明书中记载的烷基、烷氧基和除此以外的包含烷基部分的取代基将直链或支链形态全部包括在内。The alkyl group, alkoxy group, and other substituents containing an alkyl portion described in the present specification include all of linear and branched forms.
在本说明书中,烯基可以为直链或支链,碳原子数没有特别限定,但优选为2至40。根据一实施方式,上述烯基的碳原子数为2至20。根据另一实施方式,上述烯基的碳原子数为2至10。根据另一实施方式,上述烯基的碳原子数为2至6。作为具体的例子,有乙烯基、1-丙烯基、异丙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-戊烯基、2-戊烯基、3-戊烯基、3-甲基-1-丁烯基、1,3-丁二烯基、烯丙基、1-苯基乙烯-1-基、2-苯基乙烯-1-基、2,2-二苯基乙烯-1-基、2-苯基-2-(萘-1-基)乙烯-1-基、2,2-双(二苯-1-基)乙烯-1-基、茋基、苯乙烯基等,但并不限定于此。In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 6. As specific examples, there are vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthalene-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbene, styryl, etc., but are not limited thereto.
在本说明书中,上述炔基是在碳原子与碳原子之间包含三键的取代基,可以为直链或支链,碳原子数没有特别限定,但优选为2至40。根据一实施方式,上述炔基的碳原子数为2至20。根据另一实施方式,上述炔基的碳原子数为2至10。In the present specification, the alkynyl group is a substituent containing a triple bond between carbon atoms, and may be a linear or branched chain. The number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms in the alkynyl group is 2 to 20. According to another embodiment, the number of carbon atoms in the alkynyl group is 2 to 10.
在本说明书中,环烷基没有特别限定,但优选为碳原子数3至60的环烷基,根据一实施方式,上述环烷基的碳原子数为3至30。根据另一实施方式,上述环烷基的碳原子数为3至20。根据另一实施方式,上述环烷基的碳原子数为3至6。具体而言,有环丙基、环丁基、环戊基、环己基、环庚基、环辛基等,但并不限定于此。In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc., but are not limited thereto.
在本说明书中,胺基为-NH2,在上述胺基中可以取代有上述的烷基、芳基、杂环基、烯基、环烷基、以及它们的组合等。上述被取代的胺基的碳原子数没有特别限定,但优选为1至30。根据一实施方式,上述胺基的碳原子数为1至20。根据一实施方式,上述胺基的碳原子数为1至10。作为被取代的胺基的具体的例子,有甲基胺基、二甲基胺基、乙基胺基、二乙基胺基、苯基胺基、9,9-二甲基芴基苯基胺基、吡啶基苯基胺基、二苯基胺基、苯基吡啶基胺基、萘基胺基、联苯基胺基、蒽基胺基、二苯并呋喃基苯基胺基、9-甲基蒽基胺基、二苯基胺基、苯基萘基胺基、二甲苯基胺基、苯基甲苯基胺基、二苯基胺基等,但不仅限于此。In the present specification, the amino group is -NH 2 , and the above-mentioned amino group may be substituted with the above-mentioned alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and combinations thereof. The number of carbon atoms of the above-mentioned substituted amino group is not particularly limited, but is preferably 1 to 30. According to one embodiment, the number of carbon atoms of the above-mentioned amino group is 1 to 20. According to one embodiment, the number of carbon atoms of the above-mentioned amino group is 1 to 10. Specific examples of the substituted amino group include methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, 9,9-dimethylfluorenylphenylamino, pyridylphenylamino, diphenylamino, phenylpyridylamino, naphthylamino, biphenylamino, anthracenylamino, dibenzofuranylphenylamino, 9-methylanthrylamino, diphenylamino, phenylnaphthylamino, ditolylamino, phenyltolylamino, diphenylamino, etc., but are not limited thereto.
在本说明书中,芳基没有特别限定,但优选为碳原子数6至60的芳基,可以为单环芳基或多环芳基。根据一实施方式,上述芳基的碳原子数为6至30。根据一实施方式,上述芳基的碳原子数为6至20。关于上述芳基,作为单环芳基,可以为苯基、联苯基、三联苯基、四联苯基等,但并不限定于此。作为上述多环芳基,可以为萘基、蒽基、菲基、芘基、苝基、三苯基、基、芴基、三亚苯基等,但并不限定于此。In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. Regarding the aryl group, as a monocyclic aryl group, it may be phenyl, biphenyl, terphenyl, quaterphenyl, etc., but it is not limited thereto. As the polycyclic aryl group, it may be naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, triphenyl, phenylene, fluorenyl, triphenylene, etc., but are not limited to these.
在本说明书中,芴基可以被取代,2个取代基可以彼此结合而形成螺结构。这时,螺结构可以是芳香族烃环或脂肪族烃环。In the present specification, the fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure. In this case, the spiro structure may be an aromatic hydrocarbon ring or an aliphatic hydrocarbon ring.
在上述芴基被取代的情况下,可以为 等螺芴基;(9,9-二甲基芴基)和(9,9-二苯基芴基)等被取代的芴基。但并不限定于此。When the above fluorenyl group is substituted, it may be Isospirofluorenyl; (9,9-dimethylfluorenyl) and (9,9-diphenylfluorenyl) and the like substituted fluorenyl, but the present invention is not limited thereto.
在本说明书中,被取代的芳基还可以包括在芳基上稠合有脂肪族环的形态。例如,下述结构的四氢萘基被包括在被取代的芳基中。在下述结构中,苯环的碳原子中的一个可以连接到其它位置上。In this specification, substituted aryl can also include a form in which an aliphatic ring is fused to the aryl. For example, the tetrahydronaphthyl of the following structure is included in the substituted aryl. In the following structure, one of the carbon atoms of the benzene ring can be connected to other positions.
在本说明书中,芳氧基中的芳基可以适用上述的关于芳基的说明。In the present specification, the above description on the aryl group can be applied to the aryl group in the aryloxy group.
在本说明书中,上述烷基硫基和烷基磺酰基中的烷基可以适用上述的关于烷基的说明。In the present specification, the above description about the alkyl group can be applied to the alkyl group in the above alkylthio group and alkylsulfonyl group.
在本说明书中,上述芳基硫基和芳基磺酰基中的芳基可以适用上述的关于芳基的说明。In the present specification, the above description about the aryl group can be applied to the aryl group in the arylthio group and the arylsulfonyl group.
在本说明书中,杂环基是包含N、O、P、S、Si和Se中的1个以上作为杂原子的环基,碳原子数没有特别限定,但优选碳原子数为2至60。根据一实施方式,上述杂环基的碳原子数为2至30。根据一实施方式,上述杂环基的碳原子数为2至20。作为杂环基的例子,,有吡啶基、吡咯基、嘧啶基、喹啉基、哒嗪基、呋喃基、噻吩基、咪唑基、吡唑基、二苯并呋喃基、二苯并噻吩基、咔唑基、苯并咔唑基、萘并苯并呋喃基、苯并萘并噻吩基、茚并咔唑基、三嗪基等,但不仅限于此。In the present specification, the heterocyclic group is a ring group containing one or more of N, O, P, S, Si and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 2 to 60. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 20. Examples of the heterocyclic group include pyridyl, pyrrolyl, pyrimidinyl, quinolyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzocarbazolyl, naphthobenzofuranyl, benzonaphthothienyl, indenocarbazolyl, triazinyl and the like, but are not limited thereto.
在本说明书中,杂芳基为芳香族,除此以外,可以适用上述的关于杂环基的说明。In the present specification, a heteroaryl group is aromatic, and other than this, the above description about the heterocyclic group is applicable.
在本说明书中,上述亚芳基除了是2价以外,可以适用对于上述芳基的说明。In the present specification, the description of the above-mentioned aryl group is applicable to the above-mentioned arylene group except that the above-mentioned arylene group is divalent.
在本说明书中,2价的杂环除了是2价以外,可以适用对于上述杂环基的说明。In the present specification, the same explanation as for the above-mentioned heterocyclic group can be applied to the divalent heterocyclic ring except that the divalent heterocyclic ring is divalent.
在本说明书中,在与相邻的基团彼此结合而形成的取代或未取代的环中,“环”是指烃环或杂环。In the present specification, in a substituted or unsubstituted ring formed by bonding with adjacent groups, "ring" means a hydrocarbon ring or a heterocyclic ring.
上述烃环可以为芳香族、脂肪族、或者芳香族与脂肪族的稠环,可以选自上述环烷基或芳基的例示。The hydrocarbon ring may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic groups, and may be selected from the examples of the cycloalkyl group or aryl group described above.
在本说明书中,与相邻的基团彼此结合而形成环的含义是指与相邻的基团彼此结合而形成取代或未取代的脂肪族烃环、取代或未取代的芳香族烃环、取代或未取代的脂肪族杂环、取代或未取代的芳香族杂环、或者它们的稠环。上述烃环是指只由碳和氢原子构成的环。上述杂环是指包含选自N、O、P、S、Si和Se等元素中的1个以上的环。在本说明书中,上述脂肪族烃环、芳香族烃环、脂肪族杂环和芳香族杂环可以为单环或多环。In this specification, the meaning of forming a ring by combining with adjacent groups means combining with adjacent groups to form a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic heterocycle, a substituted or unsubstituted aromatic heterocycle, or a condensed ring thereof. The above hydrocarbon ring refers to a ring consisting only of carbon and hydrogen atoms. The above heterocycle refers to a ring containing one or more elements selected from N, O, P, S, Si and Se. In this specification, the above aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heterocycle and aromatic heterocycle can be monocyclic or polycyclic.
在本说明书中,脂肪族烃环是指不是芳香族的环且只由碳和氢原子构成的环。作为脂肪族烃环的例子,有环丙烷、环丁烷、环丁烯、环戊烷、环戊烯、环己烷、环己烯、1,4-环己二烯、环庚烷、环庚烯、环辛烷、环辛烯等,但并不限定于此。In this specification, an aliphatic hydrocarbon ring refers to a ring that is not an aromatic ring and is composed only of carbon and hydrogen atoms. Examples of aliphatic hydrocarbon rings include, but are not limited to, cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, and cyclooctene.
在本说明书中,芳香族烃环是指只由碳和氢原子构成的芳香族的环。作为芳香族烃环的例子,有苯、萘、蒽、菲、苝、荧蒽、三亚苯、非那烯、芘、并四苯、并五苯、芴、茚、苊烯、苯并芴、螺芴等,但并不限定于此。在本说明书中,芳香族烃环可以解释为与芳基相同的含义。In this specification, an aromatic hydrocarbon ring refers to an aromatic ring composed only of carbon and hydrogen atoms. Examples of aromatic hydrocarbon rings include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenanthene, pyrene, tetracene, In the present specification, the aromatic hydrocarbon ring can be interpreted as having the same meaning as the aryl group.
在本说明书中,脂肪族杂环是指包含杂原子中的1个以上的脂肪族环。作为脂肪族杂环的例子,有环氧乙烷(oxirane)、四氢呋喃、1,4-二烷(1,4-dioxane)、吡咯烷、哌啶、吗啉(morpholine)、氧杂环庚烷 氮杂环辛烷硫杂环辛烷等,但并不限定于此。In this specification, an aliphatic heterocycle refers to an aliphatic ring containing one or more heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dihydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane Azoctane Thioctane etc., but not limited thereto.
在本说明书中,芳香族杂环是指包含杂原子中的1个以上的芳香族环。作为芳香族杂环的例子,有吡啶、吡咯、嘧啶、哒嗪、呋喃、噻吩、咪唑、吡唑、唑、异唑、噻唑、异噻唑、三唑、二唑、噻二唑、二噻唑、四唑、吡喃、噻喃、哒嗪、嗪、噻嗪、二烯、三嗪、四嗪、异喹啉、喹啉、苯醌、喹唑啉、喹喔啉、萘啶、吖啶、菲啶、二氮杂萘、三氮杂茚、吲哚、吲哚嗪、苯并噻唑、苯并唑、苯并咪唑、苯并噻吩、苯并呋喃、二苯并噻吩、二苯并呋喃、咔唑、苯并咔唑、二苯并咔唑、吩嗪、咪唑并吡啶、吩嗪、吲哚并咔唑、茚并咔唑等,但并不限定于此。In the present specification, an aromatic heterocycle refers to an aromatic ring containing one or more heteroatoms. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, pyrazole, Azoles, Isopropylamine Azoles, thiazoles, isothiazoles, triazoles, diazole, thiadiazole, dithiazole, tetrazole, pyran, thiopyran, pyridazine, Azine, thiazine, di Olefins, triazines, tetrazines, isoquinolines, quinolines, benzoquinones, quinazolines, quinoxalines, naphthyridines, acridines, phenanthridines, naphthyridines, triazaindene, indoles, indolizines, benzothiazoles, benzo azole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, imidazopyridine, phen Oxazine, indolecarbazole, indenocarbazole, etc., but are not limited to these.
下面,详细地说明本发明的优选的实施方式。但是,,本发明的实施方式可以变形为各种形态,本发明的范围不限定于下文中说明的实施方式。Hereinafter, preferred embodiments of the present invention will be described in detail. However, the embodiments of the present invention can be modified in various forms, and the scope of the present invention is not limited to the embodiments described below.
根据本发明的由化学式1表示的化合物通过在四氢萘上连接胺基,从而可以调节化合物的HOMO和LUMO能级,调节与有机物层之间的能量屏障。The compound represented by Chemical Formula 1 according to the present invention can adjust the HOMO and LUMO energy levels of the compound by connecting an amine group to tetralin, thereby adjusting the energy barrier between the compound and the organic layer.
特别是,根据本发明的由化学式1表示的化合物通过在四氢萘上具有碳原子数1至3的烷基取代基、或者在四氢萘的苯环部分具有烷基或芳基的取代基,从而可以调节化合物的空穴迁移特性,调节器件的空穴和电子的平衡。In particular, the compound represented by Chemical Formula 1 according to the present invention has an alkyl substituent having 1 to 3 carbon atoms on tetralin, or an alkyl or aryl substituent on the benzene ring portion of tetralin, thereby adjusting the hole migration characteristics of the compound and adjusting the balance of holes and electrons in the device.
另外,根据本发明的由化学式1表示的化合物通过在被取代的芴基上连接胺基来改善空穴迁移特性,从而可以改善器件的驱动电压和效率、寿命。In addition, the compound represented by Chemical Formula 1 according to the present invention improves hole transport characteristics by connecting an amine group to the substituted fluorene group, thereby improving the driving voltage, efficiency and lifespan of the device.
因此,将由上述的化学式1表示的化合物适用于有机发光器件时,可以得到具有高效率、低电压和/或长寿命特性的有机发光器件。Therefore, when the compound represented by the above Chemical Formula 1 is applied to an organic light emitting device, an organic light emitting device having high efficiency, low voltage and/or long life characteristics may be obtained.
下面,对化学式1详细地进行说明。Next, Chemical Formula 1 will be described in detail.
[化学式1][Chemical formula 1]
在上述化学式1中,In the above chemical formula 1,
R1和R2彼此相同或不同,各自独立地为氢、氘、取代或未取代的烷基、或者取代或未取代的芳基,R1 and R2 are the same as or different from each other and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl,
R1和R2中的至少一个为碳原子数1至3的烷基,At least one of R1 and R2 is an alkyl group having 1 to 3 carbon atoms,
R2中的至少一个为取代或未取代的烷基、或者取代或未取代的芳基,At least one of R2 is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group,
R3和R4彼此相同或不同,各自独立地为氢、氘、取代或未取代的烷基、或者取代或未取代的芳基,或者与相邻的基团彼此结合而形成取代或未取代的烃环基,R3 and R4 are the same or different from each other, and are independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or are combined with adjacent groups to form a substituted or unsubstituted hydrocarbon ring group,
R5为氢、氘、取代或未取代的烷基、或者取代或未取代的芳基,R5 is hydrogen, deuterium, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl,
R3和R4为取代或未取代的芳基,或者与相邻的基团彼此结合而形成取代或未取代的烃环基时,R5中的至少一个为取代或未取代的芳基,When R3 and R4 are substituted or unsubstituted aryl groups, or when they are combined with adjacent groups to form a substituted or unsubstituted hydrocarbon ring group, at least one of R5 is a substituted or unsubstituted aryl group,
Ar1为取代或未取代的芳基、或者取代或未取代的杂环基,Ar1 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
L1和L2彼此相同或不同,各自独立地为直接键合、取代或未取代的亚芳基、或者取代或未取代的2价的杂环基,L1 and L2 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group,
a为1至8的整数,a为2以上时,R1彼此相同或不同,a is an integer from 1 to 8, and when a is 2 or more, R1 are the same or different from each other,
b为1至3的整数,b为2以上时,R2彼此相同或不同,b is an integer from 1 to 3, and when b is 2 or more, R2 are the same or different from each other,
c为1至7的整数,c为2以上时,R5彼此相同或不同。c is an integer of 1 to 7, and when c is 2 or more, R5 are the same as or different from each other.
在本说明书的一实施方式中,R1和R2彼此相同或不同,各自独立地为氢、氘、取代或未取代的烷基、或者取代或未取代的芳基。In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.
在本说明书的一实施方式中,R1和R2彼此相同或不同,各自独立地为氢、氘、取代或未取代的碳原子数1至60的烷基、或者取代或未取代的碳原子数6至60的芳基。In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
在本说明书的一实施方式中,R1和R2彼此相同或不同,各自独立地为氢、氘、取代或未取代的碳原子数1至30的烷基、或者取代或未取代的碳原子数6至30的芳基。In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
在本说明书的一实施方式中,R1和R2彼此相同或不同,各自独立地为氢、氘、取代或未取代的碳原子数1至20的烷基、或者取代或未取代的碳原子数6至20的芳基。In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
在本说明书的一实施方式中,R1和R2彼此相同或不同,各自独立地为氢、氘、取代或未取代的碳原子数1至10的烷基、或者取代或未取代的碳原子数6至12的芳基。In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
在本说明书的一实施方式中,R1和R2彼此相同或不同,各自独立地为氢、氘、被氘取代或未取代的碳原子数1至60的烷基、或者被氘取代或未取代的碳原子数6至60的芳基。In one embodiment of the present specification, R1 and R2 are the same as or different from each other and are each independently hydrogen, deuterium, an alkyl group having 1 to 60 carbon atoms which may be substituted or unsubstituted by deuterium, or an aryl group having 6 to 60 carbon atoms which may be substituted or unsubstituted by deuterium.
在本说明书的一实施方式中,R1和R2彼此相同或不同,各自独立地为氢、氘、被氘取代或未取代的碳原子数1至30的烷基、或者被氘取代或未取代的碳原子数6至30的芳基。In one embodiment of the present specification, R1 and R2 are the same as or different from each other and are independently hydrogen, deuterium, an alkyl group having 1 to 30 carbon atoms which may be substituted or unsubstituted by deuterium, or an aryl group having 6 to 30 carbon atoms which may be substituted or unsubstituted by deuterium.
在本说明书的一实施方式中,R1和R2彼此相同或不同,各自独立地为氢、氘、被氘取代或未取代的碳原子数1至20的烷基、或者被氘取代或未取代的碳原子数6至20的芳基。In one embodiment of the present specification, R1 and R2 are the same as or different from each other and are each independently hydrogen, deuterium, an alkyl group having 1 to 20 carbon atoms which may be substituted or unsubstituted by deuterium, or an aryl group having 6 to 20 carbon atoms which may be substituted or unsubstituted by deuterium.
在本说明书的一实施方式中,R1和R2彼此相同或不同,各自独立地为氢、氘、被氘取代或未取代的碳原子数1至10的烷基、或者被氘取代或未取代的碳原子数6至12的芳基。In one embodiment of the present specification, R1 and R2 are the same as or different from each other and are each independently hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms which may be substituted or unsubstituted by deuterium, or an aryl group having 6 to 12 carbon atoms which may be substituted or unsubstituted by deuterium.
在本说明书的一实施方式中,R1和R2彼此相同或不同,各自独立地为氢、氘、被氘取代或未取代的碳原子数1至3的烷基、或者被氘取代或未取代的碳原子数6至20的芳基。In one embodiment of the present specification, R1 and R2 are the same as or different from each other and are independently hydrogen, deuterium, an alkyl group having 1 to 3 carbon atoms which may be substituted or unsubstituted by deuterium, or an aryl group having 6 to 20 carbon atoms which may be substituted or unsubstituted by deuterium.
在本说明书的一实施方式中,R1和R2彼此相同或不同,各自独立地为氢、氘、被氘取代或未取代的碳原子数1至3的烷基、或者被氘取代或未取代的碳原子数6至12的芳基。In one embodiment of the present specification, R1 and R2 are the same as or different from each other and are each independently hydrogen, deuterium, an alkyl group having 1 to 3 carbon atoms which may be substituted or unsubstituted by deuterium, or an aryl group having 6 to 12 carbon atoms which may be substituted or unsubstituted by deuterium.
在本说明书的一实施方式中,R1和R2彼此相同或不同,各自独立地为氢、氘、被氘取代或未取代的碳原子数1至3的烷基、或者被氘取代或未取代的苯基。In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently hydrogen, deuterium, an alkyl group having 1 to 3 carbon atoms which may be substituted or unsubstituted by deuterium, or a phenyl group which may be substituted or unsubstituted by deuterium.
在本说明书的一实施方式中,R1和R2彼此相同或不同,各自独立地为氢、氘、碳原子数1至3的烷基、或者苯基。In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently hydrogen, deuterium, an alkyl group having 1 to 3 carbon atoms, or a phenyl group.
在本说明书的一实施方式中,R1和R2彼此相同或不同,各自独立地为氢、氘、甲基、乙基、丙基、异丙基或苯基。In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently hydrogen, deuterium, methyl, ethyl, propyl, isopropyl or phenyl.
在本说明书的一实施方式中,R1和R2彼此相同或不同,各自独立地为氢、氘、甲基、异丙基或苯基。In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently hydrogen, deuterium, methyl, isopropyl or phenyl.
在本说明书的一实施方式中,R1和R2中的至少一个为碳原子数1至3的烷基。In one embodiment of the present specification, at least one of R1 and R2 is an alkyl group having 1 to 3 carbon atoms.
在本说明书的一实施方式中,R1和R2中的至少一个为甲基、乙基或异丙基。In one embodiment of the present specification, at least one of R1 and R2 is a methyl group, an ethyl group or an isopropyl group.
在本说明书的一实施方式中,R1和R2中的至少一个为甲基或异丙基。In one embodiment of the present specification, at least one of R1 and R2 is a methyl group or an isopropyl group.
在本说明书的一实施方式中,R1和R2中的至少一个为甲基。In one embodiment of the present specification, at least one of R1 and R2 is a methyl group.
在本说明书的一实施方式中,R2中的至少一个为取代或未取代的烷基、或者取代或未取代的芳基。In one embodiment of the present specification, at least one of R2 is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.
在本说明书的一实施方式中,R2中的至少一个为取代或未取代的碳原子数1至10的烷基、或者取代或未取代的碳原子数6至20的芳基。In one embodiment of the present specification, at least one of R2 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
在本说明书的一实施方式中,R2中的至少一个为取代或未取代的碳原子数1至3的烷基、或者取代或未取代的碳原子数6至10的芳基。In one embodiment of the present specification, at least one of R2 is a substituted or unsubstituted alkyl group having 1 to 3 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms.
在本说明书的一实施方式中,R2中的至少一个为取代或未取代的碳原子数1至3的烷基、或者取代或未取代的苯基。In one embodiment of the present specification, at least one of R2 is a substituted or unsubstituted alkyl group having 1 to 3 carbon atoms, or a substituted or unsubstituted phenyl group.
在本说明书的一实施方式中,R2中的至少一个为被氘取代或未取代的碳原子数1至3的烷基、或者被氘取代或未取代的苯基。In one embodiment of the present specification, at least one of R2 is an alkyl group having 1 to 3 carbon atoms which may be substituted by deuterium or an alkyl group which may be substituted by deuterium or an phenyl group which may be substituted by deuterium.
在本说明书的一实施方式中,R2中的至少一个为碳原子数1至3的烷基、或者苯基。In one embodiment of the present specification, at least one of R2 is an alkyl group having 1 to 3 carbon atoms or a phenyl group.
在本说明书的一实施方式中,R2中的至少一个为甲基、乙基、丙基、异丙基或苯基。In one embodiment of the present specification, at least one of R2 is a methyl group, an ethyl group, a propyl group, an isopropyl group or a phenyl group.
在本说明书的一实施方式中,R2中的至少一个为甲基、异丙基或苯基。In one embodiment of the present specification, at least one of R2 is a methyl group, an isopropyl group or a phenyl group.
在本说明书的一实施方式中,R1为氢、氘或甲基,R2为氢、氘、甲基、异丙基或苯基。In one embodiment of the present specification, R1 is hydrogen, deuterium or methyl, and R2 is hydrogen, deuterium, methyl, isopropyl or phenyl.
在本说明书的一实施方式中,R1为氢或氘,R2为氢、氘、甲基或异丙基。In one embodiment of the present specification, R1 is hydrogen or deuterium, and R2 is hydrogen, deuterium, methyl or isopropyl.
在本说明书的一实施方式中,R1为氢,R2为氢、甲基或异丙基。In one embodiment of the present specification, R1 is hydrogen, and R2 is hydrogen, methyl or isopropyl.
在本说明书的一实施方式中,R1为氢,R2为氢或甲基。In one embodiment of the present specification, R1 is hydrogen, and R2 is hydrogen or methyl.
在本说明书的一实施方式中,R1为氢,R2为氢或异丙基。In one embodiment of the present specification, R1 is hydrogen, and R2 is hydrogen or isopropyl.
在本说明书的一实施方式中,R1为氢,R2为甲基或异丙基。In one embodiment of the present specification, R1 is hydrogen, and R2 is methyl or isopropyl.
在本说明书的一实施方式中,R1为氢,R2为甲基。In one embodiment of the present specification, R1 is hydrogen and R2 is methyl.
在本说明书的一实施方式中,R1为氢,R2为异丙基。In one embodiment of the present specification, R1 is hydrogen, and R2 is isopropyl.
在本说明书的一实施方式中,R1为甲基,R2为氢、氘、甲基、异丙基或苯基。In one embodiment of the present specification, R1 is a methyl group, and R2 is hydrogen, deuterium, methyl, isopropyl or phenyl.
在本说明书的一实施方式中,R1为甲基,R2为甲基或异丙基。In one embodiment of the present specification, R1 is a methyl group, and R2 is a methyl group or an isopropyl group.
在本说明书的一实施方式中,R1为甲基,R2为苯基。In one embodiment of the present specification, R1 is a methyl group, and R2 is a phenyl group.
在本说明书的一实施方式中,R3和R4彼此相同或不同,各自独立地为氢、氘、取代或未取代的烷基、或者取代或未取代的芳基,或者与相邻的基团彼此结合而形成取代或未取代的烃环基。In one embodiment of the present specification, R3 and R4 are the same or different from each other, and are independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or are combined with adjacent groups to form a substituted or unsubstituted hydrocarbon ring group.
在本说明书的一实施方式中,R3和R4彼此相同或不同,各自独立地为氢、氘、取代或未取代的碳原子数1至60的烷基、或者取代或未取代的碳原子数6至60的芳基,或者与相邻的基团彼此结合而形成取代或未取代的碳原子数6至60的烃环基。In one embodiment of the present specification, R3 and R4 are the same as or different from each other, and are independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or are combined with adjacent groups to form a substituted or unsubstituted hydrocarbon ring group having 6 to 60 carbon atoms.
在本说明书的一实施方式中,R3和R4彼此相同或不同,各自独立地为氢、氘、取代或未取代的碳原子数1至30的烷基、或者取代或未取代的碳原子数6至30的芳基,或者与相邻的基团彼此结合而形成取代或未取代的碳原子数6至30的烃环基。In one embodiment of the present specification, R3 and R4 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or are combined with adjacent groups to form a substituted or unsubstituted hydrocarbon ring group having 6 to 30 carbon atoms.
在本说明书的一实施方式中,R3和R4彼此相同或不同,各自独立地为氢、氘、取代或未取代的碳原子数1至20的烷基、或者取代或未取代的碳原子数6至20的芳基,或者与相邻的基团彼此结合而形成取代或未取代的碳原子数6至20的烃环基。In one embodiment of the present specification, R3 and R4 are the same as or different from each other, and are independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or are combined with adjacent groups to form a substituted or unsubstituted hydrocarbon ring group having 6 to 20 carbon atoms.
在本说明书的一实施方式中,R3和R4彼此相同或不同,各自独立地为氢、氘、取代或未取代的碳原子数1至10的烷基、或者取代或未取代的碳原子数6至12的芳基,或者与相邻的基团彼此结合而形成取代或未取代的碳原子数6至12的烃环基。In one embodiment of the present specification, R3 and R4 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, or are combined with adjacent groups to form a substituted or unsubstituted hydrocarbon ring group having 6 to 12 carbon atoms.
在本说明书的一实施方式中,R3和R4彼此相同或不同,各自独立地为氢、氘、被氘取代或未取代的碳原子数1至60的烷基、或者被氘取代或未取代的碳原子数6至60的芳基,或者与相邻的基团彼此结合而形成被氘取代或未取代的碳原子数6至60的烃环基。In one embodiment of the present specification, R3 and R4 are the same as or different from each other, and are independently hydrogen, deuterium, an alkyl group having 1 to 60 carbon atoms which is substituted or not substituted by deuterium, or an aryl group having 6 to 60 carbon atoms which is substituted or not substituted by deuterium, or are combined with adjacent groups to form a hydrocarbon ring group having 6 to 60 carbon atoms which is substituted or not substituted by deuterium.
在本说明书的一实施方式中,R3和R4彼此相同或不同,各自独立地为氢、氘、被氘取代或未取代的碳原子数1至30的烷基、或者被氘取代或未取代的碳原子数6至30的芳基,或者与相邻的基团彼此结合而形成被氘取代或未取代的碳原子数6至30的烃环基。In one embodiment of the present specification, R3 and R4 are the same as or different from each other, and are independently hydrogen, deuterium, an alkyl group having 1 to 30 carbon atoms which is substituted or not substituted by deuterium, or an aryl group having 6 to 30 carbon atoms which is substituted or not substituted by deuterium, or are combined with adjacent groups to form a hydrocarbon ring group having 6 to 30 carbon atoms which is substituted or not substituted by deuterium.
在本说明书的一实施方式中,R3和R4彼此相同或不同,各自独立地为氢、氘、被氘取代或未取代的碳原子数1至20的烷基、或者被氘取代或未取代的碳原子数6至20的芳基,或者与相邻的基团彼此结合而形成被氘取代或未取代的碳原子数6至20的烃环基。In one embodiment of the present specification, R3 and R4 are the same as or different from each other, and are independently hydrogen, deuterium, an alkyl group having 1 to 20 carbon atoms which is substituted or not substituted by deuterium, or an aryl group having 6 to 20 carbon atoms which is substituted or not substituted by deuterium, or are combined with adjacent groups to form a hydrocarbon ring group having 6 to 20 carbon atoms which is substituted or not substituted by deuterium.
在本说明书的一实施方式中,R3和R4彼此相同或不同,各自独立地为氢、氘、被氘取代或未取代的碳原子数1至10的烷基、或者被氘取代或未取代的碳原子数6至12的芳基,或者与相邻的基团彼此结合而形成被氘取代或未取代的碳原子数6至12的烃环基。In one embodiment of the present specification, R3 and R4 are the same as or different from each other, and are independently hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms which is substituted or not substituted by deuterium, or an aryl group having 6 to 12 carbon atoms which is substituted or not substituted by deuterium, or are combined with adjacent groups to form a hydrocarbon ring group having 6 to 12 carbon atoms which is substituted or not substituted by deuterium.
在本说明书的一实施方式中,R3和R4彼此相同或不同,各自独立地为氢、氘、被氘取代或未取代的碳原子数1至3的烷基、或者被氘取代或未取代的碳原子数6至20的芳基,或者与相邻的基团彼此结合而形成被氘取代或未取代的碳原子数6至20的烃环基。In one embodiment of the present specification, R3 and R4 are the same as or different from each other, and are independently hydrogen, deuterium, an alkyl group having 1 to 3 carbon atoms which is substituted or not substituted by deuterium, or an aryl group having 6 to 20 carbon atoms which is substituted or not substituted by deuterium, or are combined with adjacent groups to form a hydrocarbon ring group having 6 to 20 carbon atoms which is substituted or not substituted by deuterium.
在本说明书的一实施方式中,R3和R4彼此相同或不同,各自独立地为氢、氘、被氘取代或未取代的碳原子数1至3的烷基、或者被氘取代或未取代的碳原子数6至12的芳基,或者与相邻的基团彼此结合而形成被氘取代或未取代的碳原子数6至12的烃环基。In one embodiment of the present specification, R3 and R4 are the same as or different from each other, and are independently hydrogen, deuterium, an alkyl group having 1 to 3 carbon atoms which is substituted or not substituted by deuterium, or an aryl group having 6 to 12 carbon atoms which is substituted or not substituted by deuterium, or are combined with adjacent groups to form a hydrocarbon ring group having 6 to 12 carbon atoms which is substituted or not substituted by deuterium.
在本说明书的一实施方式中,R3和R4彼此相同或不同,各自独立地为氢、氘、被氘取代或未取代的碳原子数1至3的烷基、或者被氘取代或未取代的苯基,或者与相邻的基团彼此结合而形成被氘取代或未取代的螺结构。In one embodiment of the present specification, R3 and R4 are the same as or different from each other, and are independently hydrogen, deuterium, an alkyl group having 1 to 3 carbon atoms which is substituted or not substituted by deuterium, or a phenyl group which is substituted or not substituted by deuterium, or are combined with adjacent groups to form a spiro structure which is substituted or not substituted by deuterium.
在本说明书的一实施方式中,R3和R4彼此相同或不同,各自独立地为氢、氘、碳原子数1至3的烷基、或者苯基,或者与相邻的基团彼此结合而形成螺结构。In one embodiment of the present specification, R3 and R4 are the same as or different from each other, and are independently hydrogen, deuterium, an alkyl group having 1 to 3 carbon atoms, or a phenyl group, or are bonded to adjacent groups to form a spiro structure.
在本说明书的一实施方式中,R3和R4彼此相同或不同,各自独立地为氢、氘、甲基、乙基、丙基、异丙基或苯基,或者与相邻的基团彼此结合而形成螺结构。In one embodiment of the present specification, R3 and R4 are the same as or different from each other, and are independently hydrogen, deuterium, methyl, ethyl, propyl, isopropyl or phenyl, or are combined with adjacent groups to form a spiro structure.
在本说明书的一实施方式中,R3和R4彼此相同或不同,各自独立地为氢、氘、甲基或苯基,或者与相邻的基团彼此结合而形成螺结构。In one embodiment of the present specification, R3 and R4 are the same as or different from each other, and are independently hydrogen, deuterium, methyl or phenyl, or are combined with adjacent groups to form a spiro structure.
在本说明书的一实施方式中,R3和R4彼此相同或不同,各自独立地为甲基或苯基,或者与相邻的基团彼此结合而形成螺结构。In one embodiment of the present specification, R3 and R4 are the same as or different from each other, and are independently a methyl group or a phenyl group, or are combined with adjacent groups to form a spiro structure.
在本说明书的一实施方式中,上述螺结构可以形成螺芴基 In one embodiment of the present specification, the spiro structure may form a spirofluorene group.
在本说明书的一实施方式中,R5为氢、氘、取代或未取代的烷基、或者取代或未取代的芳基。In one embodiment of the present specification, R5 is hydrogen, deuterium, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl.
在本说明书的一实施方式中,R5为氢、氘、取代或未取代的碳原子数1至60的烷基、或者取代或未取代的碳原子数6至60的芳基。In one embodiment of the present specification, R5 is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
在本说明书的一实施方式中,R5为氢、氘、取代或未取代的碳原子数1至30的烷基、或者取代或未取代的碳原子数6至30的芳基。In one embodiment of the present specification, R5 is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
在本说明书的一实施方式中,R5为氢、氘、取代或未取代的碳原子数1至20的烷基、或者取代或未取代的碳原子数6至20的芳基。In one embodiment of the present specification, R5 is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
在本说明书的一实施方式中,R5为氢、氘、取代或未取代的碳原子数1至10的烷基、或者取代或未取代的碳原子数6至12的芳基。In one embodiment of the present specification, R5 is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
在本说明书的一实施方式中,R5为氢、氘、或者取代或未取代的碳原子数6至12的芳基。In one embodiment of the present specification, R5 is hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
在本说明书的一实施方式中,R5为氢、氘、被氘取代或未取代的碳原子数1至60的烷基、或者被氘取代或未取代的碳原子数6至60的芳基。In one embodiment of the present specification, R5 is hydrogen, deuterium, an alkyl group having 1 to 60 carbon atoms which may be substituted by deuterium, or an aryl group having 6 to 60 carbon atoms which may be substituted by deuterium.
在本说明书的一实施方式中,R5为氢、氘、被氘取代或未取代的碳原子数1至30的烷基、或者被氘取代或未取代的碳原子数6至30的芳基。In one embodiment of the present specification, R5 is hydrogen, deuterium, an alkyl group having 1 to 30 carbon atoms which may be substituted by deuterium, or an aryl group having 6 to 30 carbon atoms which may be substituted by deuterium.
在本说明书的一实施方式中,R5为氢、氘、被氘取代或未取代的碳原子数1至20的烷基、或者被氘取代或未取代的碳原子数6至20的芳基。In one embodiment of the present specification, R5 is hydrogen, deuterium, an alkyl group having 1 to 20 carbon atoms which may be substituted by deuterium, or an aryl group having 6 to 20 carbon atoms which may be substituted by deuterium.
在本说明书的一实施方式中,R5为氢、氘、被氘取代或未取代的碳原子数1至10的烷基、或者被氘取代或未取代的碳原子数6至12的芳基。In one embodiment of the present specification, R5 is hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms which may be substituted by deuterium, or an aryl group having 6 to 12 carbon atoms which may be substituted by deuterium.
在本说明书的一实施方式中,R5为氢、氘、或者被氘取代或未取代的碳原子数6至12的芳基。In one embodiment of the present specification, R5 is hydrogen, deuterium, or an aryl group having 6 to 12 carbon atoms which may be substituted with deuterium.
在本说明书的一实施方式中,R5为氢、氘、被氘取代或未取代的碳原子数1至3的烷基、或者被氘取代或未取代的碳原子数6至20的芳基。In one embodiment of the present specification, R5 is hydrogen, deuterium, an alkyl group having 1 to 3 carbon atoms which may be substituted by deuterium, or an aryl group having 6 to 20 carbon atoms which may be substituted by deuterium.
在本说明书的一实施方式中,R5为氢、氘、被氘取代或未取代的碳原子数1至3的烷基、或者被氘取代或未取代的碳原子数6至12的芳基。In one embodiment of the present specification, R5 is hydrogen, deuterium, an alkyl group having 1 to 3 carbon atoms which may be substituted by deuterium, or an aryl group having 6 to 12 carbon atoms which may be substituted by deuterium.
在本说明书的一实施方式中,R5为氢、氘、或者被氘取代或未取代的碳原子数6至12的芳基。In one embodiment of the present specification, R5 is hydrogen, deuterium, or an aryl group having 6 to 12 carbon atoms which may be substituted with deuterium.
在本说明书的一实施方式中,R5为氢、氘、被氘取代或未取代的苯基、被氘取代或未取代的联苯基、或者被氘取代或未取代的萘基。In one embodiment of the present specification, R5 is hydrogen, deuterium, phenyl which may be substituted by deuterium, biphenyl which may be substituted by deuterium, or naphthyl which may be substituted by deuterium.
在本说明书的一实施方式中,R5为氢、氘、苯基、联苯基或萘基。In one embodiment of the present specification, R5 is hydrogen, deuterium, phenyl, biphenyl or naphthyl.
在本说明书的一实施方式中,R3和R4为取代或未取代的芳基,或者与相邻的基团彼此结合而形成取代或未取代的烃环基时,R5中的至少一个为取代或未取代的芳基。In one embodiment of the present specification, when R3 and R4 are substituted or unsubstituted aryl groups, or when they are combined with adjacent groups to form a substituted or unsubstituted hydrocarbon ring group, at least one of R5 is a substituted or unsubstituted aryl group.
在本说明书的一实施方式中,R3和R4为取代或未取代的芳基,或者与相邻的基团彼此结合而形成取代或未取代的烃环基时,R5中的至少一个为取代或未取代的碳原子数6至60的芳基。In one embodiment of the present specification, when R3 and R4 are substituted or unsubstituted aryl groups, or when they are combined with adjacent groups to form a substituted or unsubstituted hydrocarbon ring group, at least one of R5 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
在本说明书的一实施方式中,R3和R4为取代或未取代的芳基,或者与相邻的基团彼此结合而形成取代或未取代的烃环基时,R5中的至少一个为取代或未取代的碳原子数6至30的芳基。In one embodiment of the present specification, when R3 and R4 are substituted or unsubstituted aryl groups, or when they are combined with adjacent groups to form a substituted or unsubstituted hydrocarbon ring group, at least one of R5 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
在本说明书的一实施方式中,R3和R4为取代或未取代的芳基,或者与相邻的基团彼此结合而形成取代或未取代的烃环基时,R5中的至少一个为取代或未取代的碳原子数6至20的芳基。In one embodiment of the present specification, when R3 and R4 are substituted or unsubstituted aryl groups, or when they are combined with adjacent groups to form a substituted or unsubstituted hydrocarbon ring group, at least one of R5 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
在本说明书的一实施方式中,R3和R4为取代或未取代的芳基,或者与相邻的基团彼此结合而形成取代或未取代的烃环基时,R5中的至少一个为取代或未取代的碳原子数6至12的芳基。In one embodiment of the present specification, when R3 and R4 are substituted or unsubstituted aryl groups, or when they are combined with adjacent groups to form a substituted or unsubstituted hydrocarbon ring group, at least one of R5 is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
在本说明书的一实施方式中,R3和R4为取代或未取代的芳基,或者与相邻的基团彼此结合而形成取代或未取代的烃环基时,R5中的至少一个为被氘取代或未取代的碳原子数6至30的芳基。In one embodiment of the present specification, when R3 and R4 are substituted or unsubstituted aryl groups, or when they are combined with adjacent groups to form a substituted or unsubstituted hydrocarbon ring group, at least one of R5 is a deuterium-substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
在本说明书的一实施方式中,R3和R4为取代或未取代的芳基,或者与相邻的基团彼此结合而形成取代或未取代的烃环基时,R5中的至少一个为被氘取代或未取代的碳原子数6至20的芳基。In one embodiment of the present specification, when R3 and R4 are substituted or unsubstituted aryl groups, or when they are combined with adjacent groups to form a substituted or unsubstituted hydrocarbon ring group, at least one of R5 is a deuterium-substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
在本说明书的一实施方式中,R3和R4为取代或未取代的芳基,或者与相邻的基团彼此结合而形成取代或未取代的烃环基时,R5中的至少一个为被氘取代或未取代的碳原子数6至12的芳基。In one embodiment of the present specification, when R3 and R4 are substituted or unsubstituted aryl groups, or when they are combined with adjacent groups to form a substituted or unsubstituted hydrocarbon ring group, at least one of R5 is a deuterium-substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
在本说明书的一实施方式中,R3和R4为取代或未取代的芳基,或者与相邻的基团彼此结合而形成取代或未取代的烃环基时,R5中的至少一个为被氘取代或未取代的苯基、被氘取代或未取代的联苯基、或者被氘取代或未取代的萘基。In one embodiment of the present specification, when R3 and R4 are substituted or unsubstituted aryl groups, or are combined with adjacent groups to form a substituted or unsubstituted hydrocarbon ring group, at least one of R5 is a deuterium-substituted or unsubstituted phenyl group, a deuterium-substituted or unsubstituted biphenyl group, or a deuterium-substituted or unsubstituted naphthyl group.
在本说明书的一实施方式中,R3和R4为取代或未取代的芳基,或者与相邻的基团彼此结合而形成取代或未取代的烃环基时,R5中的至少一个为苯基、联苯基或萘基。In one embodiment of the present specification, when R3 and R4 are substituted or unsubstituted aryl groups, or are combined with adjacent groups to form a substituted or unsubstituted hydrocarbon ring group, at least one of R5 is phenyl, biphenyl or naphthyl.
在本说明书的一实施方式中,L1和L2彼此相同或不同,各自独立地为直接键合、取代或未取代的亚芳基、或者取代或未取代的2价的杂环基。In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group.
在本说明书的一实施方式中,L1和L2彼此相同或不同,各自独立地为直接键合、取代或未取代的碳原子数6至60的亚芳基、或者取代或未取代的碳原子数2至60的2价的杂环基。In one embodiment of the present specification, L1 and L2 are the same as or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 2 to 60 carbon atoms.
在本说明书的一实施方式中,L1和L2彼此相同或不同,各自独立地为直接键合、取代或未取代的碳原子数6至30的亚芳基、或者取代或未取代的碳原子数2至30的2价的杂环基。In one embodiment of the present specification, L1 and L2 are the same as or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 2 to 30 carbon atoms.
在本说明书的一实施方式中,L1和L2彼此相同或不同,各自独立地为直接键合、取代或未取代的碳原子数6至20的亚芳基、或者取代或未取代的碳原子数2至20的2价的杂环基。In one embodiment of the present specification, L1 and L2 are the same as or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 2 to 20 carbon atoms.
在本说明书的一实施方式中,L1和L2彼此相同或不同,各自独立地为直接键合;取代或未取代的碳原子数6至60的亚芳基;或者取代或未取代的碳原子数2至60的含有O、S或N的2价的杂环基。In one embodiment of the present specification, L1 and L2 are the same as or different from each other and are each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted divalent heterocyclic group containing O, S or N having 2 to 60 carbon atoms.
在本说明书的一实施方式中,L1和L2彼此相同或不同,各自独立地为直接键合;取代或未取代的碳原子数6至30的亚芳基;或者取代或未取代的碳原子数2至30的含有O、S或N的2价的杂环基。In one embodiment of the present specification, L1 and L2 are the same as or different from each other and are each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted divalent heterocyclic group containing O, S or N having 2 to 30 carbon atoms.
在本说明书的一实施方式中,L1和L2彼此相同或不同,各自独立地为直接键合;取代或未取代的碳原子数6至20的亚芳基;或者取代或未取代的碳原子数2至20的含有O、S或N的2价的杂环基。In one embodiment of the present specification, L1 and L2 are the same as or different from each other and are each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted divalent heterocyclic group containing O, S or N having 2 to 20 carbon atoms.
在本说明书的一实施方式中,L1和L2彼此相同或不同,各自独立地为直接键合、或者取代或未取代的碳原子数6至30的亚芳基。In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a directly bonded or substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
在本说明书的一实施方式中,L1和L2彼此相同或不同,各自独立地为直接键合、或者被氘或烷基取代或未取代的碳原子数6至30的亚芳基。In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently an arylene group having 6 to 30 carbon atoms, which is directly bonded or substituted or unsubstituted with deuterium or an alkyl group.
在本说明书的一实施方式中,L1和L2彼此相同或不同,各自独立地为直接键合、或者被氘或碳原子数1至30的烷基取代或未取代的碳原子数6至30的亚芳基。In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond, or an arylene group having 6 to 30 carbon atoms which is substituted or unsubstituted with deuterium or an alkyl group having 1 to 30 carbon atoms.
在本说明书的一实施方式中,L1和L2彼此相同或不同,各自独立地为直接键合、取代或未取代的亚苯基、取代或未取代的亚联苯基、或者取代或未取代的2价的芴基。In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted divalent fluorenyl group.
在本说明书的一实施方式中,L1和L2彼此相同或不同,各自独立地为直接键合、或者被氘取代或未取代的碳原子数6至30的亚芳基。In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently an arylene group having 6 to 30 carbon atoms, which is directly bonded or substituted or unsubstituted with deuterium.
在本说明书的一实施方式中,L1和L2彼此相同或不同,各自独立地为直接键合、取代或未取代的亚苯基、或者取代或未取代的亚联苯基。In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.
在本说明书的一实施方式中,L1和L2彼此相同或不同,各自独立地为直接键合、被氘或烷基取代或未取代的亚苯基、或者被氘或烷基取代或未取代的亚联苯基。In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond, a phenylene group which may be substituted by deuterium or an alkyl group, or a biphenylene group which may be substituted by deuterium or an alkyl group.
在本说明书的一实施方式中,L1和L2彼此相同或不同,各自独立地为直接键合、被氘或碳原子数1至10的烷基取代或未取代的亚苯基、或者被氘或碳原子数1至10的烷基取代或未取代的亚联苯基。In one embodiment of the present specification, L1 and L2 are the same as or different from each other and are each independently a direct bond, a phenylene group substituted or unsubstituted by deuterium or an alkyl group having 1 to 10 carbon atoms, or a biphenylene group substituted or unsubstituted by deuterium or an alkyl group having 1 to 10 carbon atoms.
在本说明书的一实施方式中,L1和L2彼此相同或不同,各自独立地为直接键合、被氘或碳原子数1至3的烷基取代或未取代的亚苯基、或者被氘或碳原子数1至3的烷基取代或未取代的亚联苯基。In one embodiment of the present specification, L1 and L2 are the same as or different from each other and are each independently a direct bond, a phenylene group substituted or unsubstituted by deuterium or an alkyl group having 1 to 3 carbon atoms, or a biphenylene group substituted or unsubstituted by deuterium or an alkyl group having 1 to 3 carbon atoms.
在本说明书的一实施方式中,L1和L2彼此相同或不同,各自独立地为直接键合、被氘或甲基取代或未取代的亚苯基、或者被氘或甲基取代或未取代的亚联苯基。In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond, a phenylene group which may be substituted by deuterium or a methyl group, or a biphenylene group which may be substituted by deuterium or a methyl group.
在本说明书的一实施方式中,L1和L2彼此相同或不同,各自独立地为直接键合、被甲基取代或未取代的亚苯基、或者被甲基取代或未取代的亚联苯基。In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond, a phenylene group substituted or unsubstituted by a methyl group, or a biphenylene group substituted or unsubstituted by a methyl group.
在本说明书的一实施方式中,L1和L2彼此相同或不同,各自独立地为直接键合、被甲基取代或未取代的亚苯基、或者亚联苯基。In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond, a phenylene group which may be substituted with a methyl group, or a biphenylene group.
在本说明书的一实施方式中,L1和L2彼此相同或不同,各自独立地为直接键合、被氘取代或未取代的亚苯基、或者被氘取代或未取代的亚联苯基。In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond, a phenylene group substituted or unsubstituted by deuterium, or a biphenylene group substituted or unsubstituted by deuterium.
在本说明书的一实施方式中,L1和L2彼此相同或不同,各自独立地为直接键合、亚苯基或亚联苯基。In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond, a phenylene group, or a biphenylene group.
在本说明书的一实施方式中,L1和L2彼此相同,L1和L2为直接键合、或者取代或未取代的苯基。In one embodiment of the present specification, L1 and L2 are the same as each other, and L1 and L2 are directly bonded to each other or are substituted or unsubstituted phenyl groups.
在本说明书的一实施方式中,L1和L2彼此相同,L1和L2为直接键合、或者被氘取代或未取代的苯基。In one embodiment of the present specification, L1 and L2 are the same as each other, and L1 and L2 are directly bonded to each other, or are phenyl groups which may be substituted with deuterium or not.
在本说明书的一实施方式中,L1和L2彼此相同,L1和L2为直接键合或苯基。In one embodiment of the present specification, L1 and L2 are the same as each other, and L1 and L2 are a direct bond or a phenyl group.
在本说明书的一实施方式中,L1和L2彼此相同,L1和L2为直接键合。In one embodiment of the present specification, L1 and L2 are identical to each other, and L1 and L2 are directly bonded to each other.
在本说明书的一实施方式中,L1为直接键合、或者取代或未取代的苯基。In one embodiment of the present specification, L1 is a direct bond, or a substituted or unsubstituted phenyl group.
在本说明书的一实施方式中,L1为直接键合、或者被氘取代或未取代的苯基。In one embodiment of the present specification, L1 is a phenyl group which is directly bonded or substituted or unsubstituted with deuterium.
在本说明书的一实施方式中,L1为直接键合或苯基。In one embodiment of the present specification, L1 is a direct bond or a phenyl group.
在本说明书的一实施方式中,L1为直接键合。In one embodiment of the present specification, L1 is a direct bond.
在本说明书的一实施方式中,L2彼此相同或不同,各自独立地为直接键合、取代或未取代的亚苯基、或者取代或未取代的亚联苯基。In one embodiment of the present specification, L2 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.
在本说明书的一实施方式中,L2彼此相同或不同,各自独立地为直接键合、被氘或烷基取代或未取代的亚苯基、或者被氘或烷基取代或未取代的亚联苯基。In one embodiment of the present specification, L2 are the same as or different from each other, and are each independently a direct bond, a phenylene group which may be substituted by deuterium or an alkyl group, or a biphenylene group which may be substituted by deuterium or an alkyl group.
在本说明书的一实施方式中,L2彼此相同或不同,各自独立地为直接键合、被氘或甲基取代或未取代的亚苯基、或者被氘或甲基取代或未取代的亚联苯基。In one embodiment of the present specification, L2 are the same as or different from each other, and are each independently a direct bond, a phenylene group which may be substituted by deuterium or a methyl group, or a biphenylene group which may be substituted by deuterium or a methyl group.
在本说明书的一实施方式中,L2彼此相同或不同,各自独立地为直接键合、被甲基取代或未取代的亚苯基、或者亚联苯基。In one embodiment of the present specification, L2 are the same as or different from each other, and are each independently a direct bond, a phenylene group which may be substituted with a methyl group, or a biphenylene group.
在本说明书的一实施方式中,L2彼此相同或不同,各自独立地为直接键合、亚苯基或亚联苯基。In one embodiment of the present specification, L2 are the same as or different from each other, and are each independently a direct bond, a phenylene group, or a biphenylene group.
在本说明书的一实施方式中,L2为直接键合。In one embodiment of the present specification, L2 is a direct bond.
在本说明书的一实施方式中,Ar1为取代或未取代的芳基、或者取代或未取代的杂环基。In one embodiment of the present specification, Ar1 is a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.
在本说明书的一实施方式中,Ar1为取代或未取代的碳原子数6至60的亚芳基、或者取代或未取代的碳原子数2至60的杂环基。In one embodiment of the present specification, Ar1 is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
在本说明书的一实施方式中,Ar1为取代或未取代的碳原子数6至30的亚芳基、或者取代或未取代的碳原子数2至30的杂环基。In one embodiment of the present specification, Ar1 is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
在本说明书的一实施方式中,Ar1为取代或未取代的碳原子数6至60的亚芳基;或者取代或未取代的碳原子数2至60的含有O、S或N的杂环基。In one embodiment of the present specification, Ar1 is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group containing O, S or N having 2 to 60 carbon atoms.
在本说明书的一实施方式中,Ar1为取代或未取代的碳原子数6至30的亚芳基;或者取代或未取代的碳原子数2至30的含有O、S或N的杂环基。In one embodiment of the present specification, Ar1 is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group containing O, S or N having 2 to 30 carbon atoms.
在本说明书的一实施方式中,Ar1为被氘、碳原子数1至30的烷基或碳原子数6至30的芳基取代或未取代的碳原子数6至60的亚芳基;或者被氘、碳原子数1至30的烷基或碳原子数6至30的芳基取代或未取代的碳原子数2至60的含有O、S或N的杂环基。In one embodiment of the present specification, Ar1 is an arylene group having 6 to 60 carbon atoms, which is unsubstituted or substituted by deuterium, an alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms; or a heterocyclic group containing O, S or N having 2 to 60 carbon atoms, which is unsubstituted or substituted by deuterium, an alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms.
在本说明书的一实施方式中,Ar1为被氘、碳原子数1至30的烷基或碳原子数6至30的芳基取代或未取代的碳原子数6至30的亚芳基;或者被氘、碳原子数1至30的烷基或碳原子数6至30的芳基取代或未取代的碳原子数2至30的含有O、S或N的杂环基。In one embodiment of the present specification, Ar1 is an arylene group having 6 to 30 carbon atoms, which is unsubstituted or substituted by deuterium, an alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms; or a heterocyclic group containing O, S or N having 2 to 30 carbon atoms, which is unsubstituted or substituted by deuterium, an alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms.
在本说明书的一实施方式中,Ar1为被氘、碳原子数1至20的烷基或碳原子数6至20的芳基取代或未取代的碳原子数6至30的亚芳基;或者被氘、碳原子数1至20的烷基或碳原子数6至20的芳基取代或未取代的碳原子数2至30的含有O、S或N的杂环基。In one embodiment of the present specification, Ar1 is an arylene group having 6 to 30 carbon atoms, which is unsubstituted or substituted by deuterium, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms; or a heterocyclic group containing O, S or N having 2 to 30 carbon atoms, which is unsubstituted or substituted by deuterium, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms.
在本说明书的一实施方式中,Ar1为被氘、碳原子数1至10的烷基或碳原子数6至12的芳基取代或未取代的碳原子数6至30的亚芳基;或者被氘、碳原子数1至10的烷基或碳原子数6至12的芳基取代或未取代的碳原子数2至30的含有O、S或N的杂环基。In one embodiment of the present specification, Ar1 is an arylene group having 6 to 30 carbon atoms, which is unsubstituted or substituted by deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms; or a heterocyclic group containing O, S or N having 2 to 30 carbon atoms, which is unsubstituted or substituted by deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms.
在本说明书的一实施方式中,Ar1为被氘、碳原子数1至3的烷基或碳原子数6至10的芳基取代或未取代的碳原子数6至30的亚芳基;或者被氘、碳原子数1至3的烷基或碳原子数6至10的芳基取代或未取代的碳原子数2至30的含有O、S或N的杂环基。In one embodiment of the present specification, Ar1 is an arylene group having 6 to 30 carbon atoms, which is unsubstituted or substituted by deuterium, an alkyl group having 1 to 3 carbon atoms, or an aryl group having 6 to 10 carbon atoms; or a heterocyclic group containing O, S or N having 2 to 30 carbon atoms, which is unsubstituted or substituted by deuterium, an alkyl group having 1 to 3 carbon atoms, or an aryl group having 6 to 10 carbon atoms.
在本说明书的一实施方式中,Ar1为被氘、碳原子数1至10的烷基或碳原子数6至12的芳基取代或未取代的碳原子数6至20的亚芳基;或者被氘、碳原子数1至10的烷基或碳原子数6至12的芳基取代或未取代的碳原子数2至20的含有O、S或N的杂环基。In one embodiment of the present specification, Ar1 is an arylene group having 6 to 20 carbon atoms, which is unsubstituted or substituted by deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms; or a heterocyclic group containing O, S or N having 2 to 20 carbon atoms, which is unsubstituted or substituted by deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms.
在本说明书的一实施方式中,Ar1为被氘、碳原子数1至3的烷基或碳原子数6至10的芳基取代或未取代的碳原子数6至20的亚芳基;或者被氘、碳原子数1至3的烷基或碳原子数6至10的芳基取代或未取代的碳原子数2至20的含有O、S或N的杂环基。In one embodiment of the present specification, Ar1 is an arylene group having 6 to 20 carbon atoms, which is unsubstituted or substituted by deuterium, an alkyl group having 1 to 3 carbon atoms, or an aryl group having 6 to 10 carbon atoms; or a heterocyclic group containing O, S or N having 2 to 20 carbon atoms, which is unsubstituted or substituted by deuterium, an alkyl group having 1 to 3 carbon atoms, or an aryl group having 6 to 10 carbon atoms.
在本说明书的一实施方式中,Ar1为被氘、碳原子数1至10的烷基或碳原子数6至12的芳基取代或未取代的碳原子数6至20的亚芳基;或者被氘取代或未取代的碳原子数2至20的含有O、S或N的杂环基。In one embodiment of the present specification, Ar1 is an arylene group having 6 to 20 carbon atoms, which is unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms; or a heterocyclic group containing O, S or N having 2 to 20 carbon atoms, which is unsubstituted or substituted with deuterium.
在本说明书的一实施方式中,Ar1为被氘、碳原子数1至3的烷基或碳原子数6至10的芳基取代或未取代的碳原子数6至20的亚芳基;或者被氘取代或未取代的碳原子数2至20的含有O、S或N的杂环基。In one embodiment of the present specification, Ar1 is an arylene group having 6 to 20 carbon atoms, which is unsubstituted or substituted with deuterium, an alkyl group having 1 to 3 carbon atoms, or an aryl group having 6 to 10 carbon atoms; or a heterocyclic group containing O, S or N having 2 to 20 carbon atoms, which is unsubstituted or substituted with deuterium.
在本说明书的一实施方式中,Ar1为取代或未取代的苯基、取代或未取代的联苯基、取代或未取代的三联苯基、取代或未取代的萘基、取代或未取代的菲基、取代或未取代的三亚苯基、取代或未取代的四氢萘基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、或者取代或未取代的咔唑基。In one embodiment of the present specification, Ar1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted tetrahydronaphthyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.
在本说明书的一实施方式中,Ar1为取代或未取代的苯基、取代或未取代的联苯基、取代或未取代的三联苯基、取代或未取代的萘基、取代或未取代的菲基、取代或未取代的四氢萘基、取代或未取代的二苯并呋喃基、或者取代或未取代的二苯并噻吩基。In one embodiment of the present specification, Ar1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted tetrahydronaphthyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.
在本说明书的一实施方式中,Ar1为被氘取代或未取代的苯基;被氘取代或未取代的联苯基;被氘取代或未取代的三联苯基;被氘取代或未取代的萘基;被氘取代或未取代的菲基;被由氘、碳原子数1至10的烷基和碳原子数6至20的芳基组成的组中的1个以上的取代基取代或未取代的四氢萘基;被氘取代或未取代的二苯并呋喃基;或者被氘取代或未取代的二苯并噻吩基。In one embodiment of the present specification, Ar1 is phenyl substituted or unsubstituted by deuterium; biphenyl substituted or unsubstituted by deuterium; terphenyl substituted or unsubstituted by deuterium; naphthyl substituted or unsubstituted by deuterium; phenanthryl substituted or unsubstituted by deuterium; tetrahydronaphthyl substituted or unsubstituted by one or more substituents selected from the group consisting of deuterium, alkyl having 1 to 10 carbon atoms, and aryl having 6 to 20 carbon atoms; dibenzofuranyl substituted or unsubstituted by deuterium; or dibenzothiophene substituted or unsubstituted by deuterium.
在本说明书的一实施方式中,Ar1为被氘取代或未取代的苯基;被氘取代或未取代的联苯基;被氘取代或未取代的三联苯基;被氘取代或未取代的萘基;被氘取代或未取代的菲基;被由氘、碳原子数1至3的烷基和碳原子数6至12的芳基组成的组中的1个以上的取代基取代或未取代的四氢萘基;被氘取代或未取代的二苯并呋喃基;或者被氘取代或未取代的二苯并噻吩基。In one embodiment of the present specification, Ar1 is phenyl substituted or unsubstituted by deuterium; biphenyl substituted or unsubstituted by deuterium; terphenyl substituted or unsubstituted by deuterium; naphthyl substituted or unsubstituted by deuterium; phenanthryl substituted or unsubstituted by deuterium; tetrahydronaphthyl substituted or unsubstituted by one or more substituents selected from the group consisting of deuterium, alkyl having 1 to 3 carbon atoms, and aryl having 6 to 12 carbon atoms; dibenzofuranyl substituted or unsubstituted by deuterium; or dibenzothiophene substituted or unsubstituted by deuterium.
在本说明书的一实施方式中,Ar1为被氘取代或未取代的苯基;被氘取代或未取代的联苯基;被氘取代或未取代的三联苯基;被氘取代或未取代的萘基;被氘取代或未取代的菲基;被由氘、甲基、异丙基和苯基组成的组中的1个以上的取代基取代或未取代的四氢萘基;被氘取代或未取代的二苯并呋喃基;或者被氘取代或未取代的二苯并噻吩基。In one embodiment of the present specification, Ar1 is phenyl substituted or unsubstituted by deuterium; biphenyl substituted or unsubstituted by deuterium; terphenyl substituted or unsubstituted by deuterium; naphthyl substituted or unsubstituted by deuterium; phenanthryl substituted or unsubstituted by deuterium; tetrahydronaphthyl substituted or unsubstituted by one or more substituents selected from the group consisting of deuterium, methyl, isopropyl and phenyl; dibenzofuranyl substituted or unsubstituted by deuterium; or dibenzothiophene substituted or unsubstituted by deuterium.
在本说明书的一实施方式中,Ar1为苯基;联苯基;三联苯基;萘基;菲基;三亚苯基;被由甲基、异丙基和苯基组成的组中的1个以上的取代基取代或未取代的四氢萘基;二苯并呋喃基;二苯并噻吩基;或者咔唑基。In one embodiment of the present specification, Ar1 is phenyl; biphenyl; terphenyl; naphthyl; phenanthryl; triphenylene; tetrahydronaphthyl which may be substituted or unsubstituted with one or more substituents selected from the group consisting of methyl, isopropyl and phenyl; dibenzofuranyl; dibenzothienyl; or carbazolyl.
在本说明书的一实施方式中,Ar1为苯基;联苯基;三联苯基;萘基;菲基;被由甲基、异丙基和苯基组成的组中的1个以上的取代基取代或未取代的四氢萘基;二苯并呋喃基;或者二苯并噻吩基。In one embodiment of the present specification, Ar1 is phenyl; biphenyl; terphenyl; naphthyl; phenanthryl; tetrahydronaphthyl which may be substituted or unsubstituted by one or more substituents selected from the group consisting of methyl, isopropyl and phenyl; dibenzofuranyl; or dibenzothiophenyl.
在本说明书的一实施方式中,a为1至8的整数。In one embodiment of the present specification, a is an integer of 1 to 8.
在本说明书的一实施方式中,a为1至4的整数。In one embodiment of the present specification, a is an integer of 1 to 4.
在本说明书的一实施方式中,a为8。In one embodiment of the present specification, a is 8.
在本说明书的一实施方式中,a为7。In one embodiment of the present specification, a is 7.
在本说明书的一实施方式中,a为6。In one embodiment of the present specification, a is 6.
在本说明书的一实施方式中,a为5。In one embodiment of the present specification, a is 5.
在本说明书的一实施方式中,a为4。In one embodiment of the present specification, a is 4.
在本说明书的一实施方式中,a为3。In one embodiment of the present specification, a is 3.
在本说明书的一实施方式中,a为2。In one embodiment of the present specification, a is 2.
在本说明书的一实施方式中,a为1。In one embodiment of the present specification, a is 1.
在本说明书的一实施方式中,b为1至3的整数。In one embodiment of the present specification, b is an integer of 1 to 3.
在本说明书的一实施方式中,b为3。In one embodiment of the present specification, b is 3.
在本说明书的一实施方式中,b为2。In one embodiment of the present specification, b is 2.
在本说明书的一实施方式中,b为1。In one embodiment of the present specification, b is 1.
在本说明书的一实施方式中,c为1至7的整数。In one embodiment of the present specification, c is an integer of 1 to 7.
在本说明书的一实施方式中,c为7。In one embodiment of the present specification, c is 7.
在本说明书的一实施方式中,c为6。In one embodiment of the present specification, c is 6.
在本说明书的一实施方式中,c为5。In one embodiment of the present specification, c is 5.
在本说明书的一实施方式中,c为4。In one embodiment of the present specification, c is 4.
在本说明书的一实施方式中,c为3。In one embodiment of the present specification, c is 3.
在本说明书的一实施方式中,c为2。In one embodiment of the present specification, c is 2.
在本说明书的一实施方式中,c为1。In one embodiment of the present specification, c is 1.
在本说明书的一实施方式中,上述化学式1由下述化学式2表示。In one embodiment of the present specification, the above Chemical Formula 1 is represented by the following Chemical Formula 2.
[化学式2][Chemical formula 2]
在上述化学式2中,In the above chemical formula 2,
R1至R5、L1、L2、Ar1和a至c的定义与上述化学式1中的定义相同。Definitions of R1 to R5, L1, L2, Ar1, and a to c are the same as those in the above Chemical Formula 1.
在本说明书的一实施方式中,上述化学式1由下述化学式3表示。In one embodiment of the present specification, the above Chemical Formula 1 is represented by the following Chemical Formula 3.
[化学式3][Chemical formula 3]
在上述化学式3中,In the above chemical formula 3,
R1、R2、L1、L2、Ar1、a和b的定义与上述化学式1中的定义相同,R1, R2, L1, L2, Ar1, a and b are defined as in the above chemical formula 1,
R3和R4彼此相同或不同,各自独立地为氢、氘、取代或未取代的烷基、或者取代或未取代的芳基,或者与相邻的基团彼此结合而形成取代或未取代的烃环基,R3 and R4 are the same or different from each other, and are independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or are combined with adjacent groups to form a substituted or unsubstituted hydrocarbon ring group,
R5'为氢、氘、取代或未取代的烷基、或者取代或未取代的芳基,R5' is hydrogen, deuterium, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl,
R3和R4为取代或未取代的芳基,或者与相邻的基团彼此结合而形成取代或未取代的烃环基时,R5'为取代或未取代的芳基。When R3 and R4 are substituted or unsubstituted aryl groups, or when they are combined with adjacent groups to form a substituted or unsubstituted hydrocarbon ring group, R5' is a substituted or unsubstituted aryl group.
在本说明书的一实施方式中,R5'为氢、氘、取代或未取代的碳原子数1至60的烷基、或者取代或未取代的碳原子数6至60的芳基。In one embodiment of the present specification, R5' is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
在本说明书的一实施方式中,R5'为氢、氘、取代或未取代的碳原子数1至30的烷基、或者取代或未取代的碳原子数6至30的芳基。In one embodiment of the present specification, R5' is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
在本说明书的一实施方式中,R5'为氢、氘、取代或未取代的碳原子数1至20的烷基、或者取代或未取代的碳原子数6至20的芳基。In one embodiment of the present specification, R5' is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
在本说明书的一实施方式中,R5'为氢、氘、取代或未取代的碳原子数1至10的烷基、或者取代或未取代的碳原子数6至12的芳基。In one embodiment of the present specification, R5' is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
在本说明书的一实施方式中,R5'为氢、氘、或者取代或未取代的碳原子数6至12的芳基。In one embodiment of the present specification, R5' is hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
在本说明书的一实施方式中,R5'为氢、氘、被氘取代或未取代的碳原子数1至60的烷基、或者被氘取代或未取代的碳原子数6至60的芳基。In one embodiment of the present specification, R5′ is hydrogen, deuterium, an alkyl group having 1 to 60 carbon atoms which may be substituted by deuterium, or an aryl group having 6 to 60 carbon atoms which may be substituted by deuterium.
在本说明书的一实施方式中,R5'为氢、氘、被氘取代或未取代的碳原子数1至30的烷基、或者被氘取代或未取代的碳原子数6至30的芳基。In one embodiment of the present specification, R5' is hydrogen, deuterium, an alkyl group having 1 to 30 carbon atoms which may be substituted by deuterium, or an aryl group having 6 to 30 carbon atoms which may be substituted by deuterium.
在本说明书的一实施方式中,R5'为氢、氘、被氘取代或未取代的碳原子数1至20的烷基、或者被氘取代或未取代的碳原子数6至20的芳基。In one embodiment of the present specification, R5′ is hydrogen, deuterium, an alkyl group having 1 to 20 carbon atoms which may be substituted by deuterium, or an aryl group having 6 to 20 carbon atoms which may be substituted by deuterium.
在本说明书的一实施方式中,R5'为氢、氘、被氘取代或未取代的碳原子数1至10的烷基、或者被氘取代或未取代的碳原子数6至12的芳基。In one embodiment of the present specification, R5' is hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms which may be substituted by deuterium, or an aryl group having 6 to 12 carbon atoms which may be substituted by deuterium.
在本说明书的一实施方式中,R5'为氢、氘、或者被氘取代或未取代的碳原子数6至12的芳基。In one embodiment of the present specification, R5' is hydrogen, deuterium, or an aryl group having 6 to 12 carbon atoms which may be substituted with deuterium.
在本说明书的一实施方式中,R5'为氢、氘、被氘取代或未取代的碳原子数1至3的烷基、或者被氘取代或未取代的碳原子数6至20的芳基。In one embodiment of the present specification, R5' is hydrogen, deuterium, an alkyl group having 1 to 3 carbon atoms which may be substituted by deuterium, or an aryl group having 6 to 20 carbon atoms which may be substituted by deuterium.
在本说明书的一实施方式中,R5'为氢、氘、被氘取代或未取代的碳原子数1至3的烷基、或者被氘取代或未取代的碳原子数6至12的芳基。In one embodiment of the present specification, R5′ is hydrogen, deuterium, an alkyl group having 1 to 3 carbon atoms which may be substituted by deuterium, or an aryl group having 6 to 12 carbon atoms which may be substituted by deuterium.
在本说明书的一实施方式中,R5'为氢、氘、或者被氘取代或未取代的碳原子数6至12的芳基。In one embodiment of the present specification, R5' is hydrogen, deuterium, or an aryl group having 6 to 12 carbon atoms which may be substituted with deuterium.
在本说明书的一实施方式中,R5'为氢、氘、被氘取代或未取代的苯基、被氘取代或未取代的联苯基、或者被氘取代或未取代的萘基。In one embodiment of the present specification, R5′ is hydrogen, deuterium, phenyl which may be substituted by deuterium, biphenyl which may be substituted by deuterium, or naphthyl which may be substituted by deuterium.
在本说明书的一实施方式中,R5'为氢、氘、苯基、联苯基或萘基。In one embodiment of the present specification, R5' is hydrogen, deuterium, phenyl, biphenyl or naphthyl.
在本说明书的一实施方式中,上述化学式1由下述化学式1-1表示。In one embodiment of the present specification, the above Chemical Formula 1 is represented by the following Chemical Formula 1-1.
[化学式1-1][Chemical formula 1-1]
在上述化学式1-1中,In the above chemical formula 1-1,
R1、R3至R5、L1、L2、Ar1、a和c的定义与上述化学式1中的定义相同,R1, R3 to R5, L1, L2, Ar1, a and c are defined as in the above Chemical Formula 1,
R2'为取代或未取代的烷基、或者取代或未取代的芳基。R2' is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.
在本说明书的一实施方式中,R2'为取代或未取代的碳原子数1至60的烷基、或者取代或未取代的碳原子数6至60的芳基。In one embodiment of the present specification, R2′ is a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
在本说明书的一实施方式中,R2'为取代或未取代的碳原子数1至30的烷基、或者取代或未取代的碳原子数6至30的芳基。In one embodiment of the present specification, R2′ is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
在本说明书的一实施方式中,R2'为取代或未取代的碳原子数1至20的烷基、或者取代或未取代的碳原子数6至20的芳基。In one embodiment of the present specification, R2' is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
在本说明书的一实施方式中,R2'为取代或未取代的碳原子数1至10的烷基、或者取代或未取代的碳原子数6至12的芳基。In one embodiment of the present specification, R2′ is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
在本说明书的一实施方式中,R2'为取代或未取代的碳原子数1至3的烷基、或者取代或未取代的碳原子数6至10的芳基。In one embodiment of the present specification, R2′ is a substituted or unsubstituted alkyl group having 1 to 3 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms.
在本说明书的一实施方式中,R2'为取代或未取代的碳原子数1至3的烷基、或者取代或未取代的苯基。In one embodiment of the present specification, R2' is a substituted or unsubstituted alkyl group having 1 to 3 carbon atoms, or a substituted or unsubstituted phenyl group.
在本说明书的一实施方式中,R2'为被氘取代或未取代的碳原子数1至60的烷基、或者被氘取代或未取代的碳原子数6至60的芳基。In one embodiment of the present specification, R2′ is an alkyl group having 1 to 60 carbon atoms which may be substituted by deuterium, or an aryl group having 6 to 60 carbon atoms which may be substituted by deuterium.
在本说明书的一实施方式中,R2'为被氘取代或未取代的碳原子数1至30的烷基、或者被氘取代或未取代的碳原子数6至30的芳基。In one embodiment of the present specification, R2′ is an alkyl group having 1 to 30 carbon atoms which may be substituted by deuterium, or an aryl group having 6 to 30 carbon atoms which may be substituted by deuterium.
在本说明书的一实施方式中,R2'为被氘取代或未取代的碳原子数1至20的烷基、或者被氘取代或未取代的碳原子数6至20的芳基。In one embodiment of the present specification, R2′ is an alkyl group having 1 to 20 carbon atoms which may be substituted by deuterium, or an aryl group having 6 to 20 carbon atoms which may be substituted by deuterium.
在本说明书的一实施方式中,R2'为被氘取代或未取代的碳原子数1至10的烷基、或者被氘取代或未取代的碳原子数6至12的芳基。In one embodiment of the present specification, R2′ is an alkyl group having 1 to 10 carbon atoms which may be substituted by deuterium, or an aryl group having 6 to 12 carbon atoms which may be substituted by deuterium.
在本说明书的一实施方式中,R2'为被氘取代或未取代的碳原子数1至3的烷基、或者被氘取代或未取代的碳原子数6至10的芳基。In one embodiment of the present specification, R2′ is an alkyl group having 1 to 3 carbon atoms which may be substituted by deuterium, or an aryl group having 6 to 10 carbon atoms which may be substituted by deuterium.
在本说明书的一实施方式中,R2'为被氘取代或未取代的碳原子数1至3的烷基、或者被氘取代或未取代的苯基。In one embodiment of the present specification, R2′ is an alkyl group having 1 to 3 carbon atoms which may be substituted by deuterium or an alkyl group which may be substituted by deuterium or an phenyl group which may be substituted by deuterium.
在本说明书的一实施方式中,R2'为甲基、乙基、丙基、异丙基、或者被氘取代或未取代的苯基。In one embodiment of the present specification, R2′ is a methyl group, an ethyl group, a propyl group, an isopropyl group, or a phenyl group which may be substituted with deuterium.
在本说明书的一实施方式中,R2'为甲基、乙基、丙基、异丙基或苯基。In one embodiment of the present specification, R2' is a methyl group, an ethyl group, a propyl group, an isopropyl group or a phenyl group.
在本说明书的一实施方式中,R2'为甲基、异丙基或苯基。In one embodiment of the present specification, R2' is a methyl group, an isopropyl group or a phenyl group.
在本说明书的一实施方式中,R2'为甲基或苯基。In one embodiment of the present specification, R2' is a methyl group or a phenyl group.
在本说明书的一实施方式中,上述化学式1由下述化学式2-1至2-3中的任一个表示。In one embodiment of the present specification, the above Chemical Formula 1 is represented by any one of the following Chemical Formulas 2-1 to 2-3.
[化学式2-1][Chemical formula 2-1]
[化学式2-2][Chemical formula 2-2]
[化学式2-3][Chemical formula 2-3]
在上述化学式2-1至2-3中,In the above chemical formulas 2-1 to 2-3,
R1至R5、L1、L2、Ar1、a至c的定义与上述化学式1中的定义相同。Definitions of R1 to R5, L1, L2, Ar1, and a to c are the same as those in the above Chemical Formula 1.
在本说明书的一实施方式中,上述化学式1由下述化学式2-1、2-2和2-3-1中的任一个表示。In one embodiment of the present specification, the above Chemical Formula 1 is represented by any one of the following Chemical Formulas 2-1, 2-2, and 2-3-1.
[化学式2-1][Chemical formula 2-1]
[化学式2-2][Chemical formula 2-2]
[化学式2-3-1][Chemical formula 2-3-1]
在上述化学式2-1、2-2和2-3-1中,In the above chemical formulas 2-1, 2-2 and 2-3-1,
R1至R5、L1、L2、Ar1和a至c的定义与上述化学式1中的定义相同。Definitions of R1 to R5, L1, L2, Ar1, and a to c are the same as those in the above Chemical Formula 1.
在本说明书的一实施方式中,上述化学式1由下述化学式3-1或3-2表示。In one embodiment of the present specification, the above Chemical Formula 1 is represented by the following Chemical Formula 3-1 or 3-2.
[化学式3-1][Chemical formula 3-1]
[化学式3-2][Chemical formula 3-2]
在上述化学式3-1和3-2中,In the above chemical formulas 3-1 and 3-2,
R1至R5、L1、L2、Ar1和a至c的定义与上述化学式1中的定义相同。Definitions of R1 to R5, L1, L2, Ar1, and a to c are the same as those in the above Chemical Formula 1.
在本说明书的一实施方式中,上述化学式1由下述化合物中的任一个表示。In one embodiment of the present specification, the above Chemical Formula 1 is represented by any one of the following compounds.
根据本说明书的一实施方式的由化学式1表示的化合物可以如下述反应式1那样制造核结构。取代基可以通过本技术领域中已知的方法进行结合,取代基的种类、位置或个数可以根据本技术领域中已知的技术进行变更。The compound represented by Chemical Formula 1 according to one embodiment of the present specification can produce a core structure as shown in the following Reaction Formula 1. Substituents can be bonded by methods known in the art, and the type, position or number of substituents can be changed according to techniques known in the art.
<反应式1><Reaction formula 1>
在上述反应式1中,R1至R5、L1、L2、Ar1和a至c的定义与上述的化学式1中的定义相同。In the above Reaction Formula 1, the definitions of R1 to R5, L1, L2, Ar1, and a to c are the same as those in the above Chemical Formula 1.
在上述反应式1中,X可以为Cl、Br、I等卤素基团。In the above reaction formula 1, X can be a halogen group such as Cl, Br, I, etc.
在上述反应式1中,例示了合成在特定位置上结合有特定取代基的化合物的过程,但可以利用本技术领域中已知的起始物质、中间物质等并通过本技术领域中已知的合成方法来合成属于上述化学式1的范围的化合物。In the above reaction formula 1, a process for synthesizing a compound having a specific substituent bonded to a specific position is illustrated, but compounds falling within the scope of the above chemical formula 1 can be synthesized using starting materials, intermediate materials, etc. known in the technical field and by synthesis methods known in the technical field.
在本说明书中,通过在由上述化学式1表示的化合物的核结构中导入各种取代基,从而可以合成具有各种能带隙的化合物。此外,在本说明书中,通过在如上所示的结构的核结构中导入各种取代基,从而还可以调节化合物的HOMO和LUMO能级。In the present specification, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure of the compound represented by the above Chemical Formula 1. In addition, in the present specification, the HOMO and LUMO energy levels of the compound can also be adjusted by introducing various substituents into the core structure of the structure shown above.
另外,本说明书提供包含上面提到的化合物的有机发光器件。In addition, the present specification provides an organic light-emitting device including the above-mentioned compound.
在本说明书中,当指出某一构件位于另一个构件“上”时,其不仅包括某一构件与另一构件相接的情况,还包括两构件之间存在其它构件的情况。In the present specification, when it is mentioned that a certain component is located “on” another component, it not only includes the case where the certain component is in contact with the other component, but also includes the case where other components exist between the two components.
在本说明书中,当指出某一部分“包括/包含”某一构成要素时,只要没有特别相反的记载,则意味着可以进一步包括其它构成要素,而不是将其它构成要素排除。In the present specification, when it is indicated that a certain part “includes/comprises” a certain constituent element, unless there is a particular description to the contrary, it means that other constituent elements may be further included, rather than excluding other constituent elements.
根据本说明书的有机发光器件的特征在于,包括:阳极、阴极、以及设置在上述阳极与上述阴极之间的1层以上的有机物层,上述有机物层中的1层以上包含由上述的化学式1表示的化合物。The organic light-emitting device according to the present specification is characterized by comprising: an anode, a cathode, and one or more organic layers disposed between the anode and the cathode, wherein one or more of the organic layers contains the compound represented by the above Chemical Formula 1.
本说明书的有机发光器件利用上述的化学式1的化合物形成有机物层,除此以外,可以利用通常的有机发光器件的制造方法和材料来制造。The organic light-emitting device of the present specification uses the compound of Chemical Formula 1 to form an organic layer, and can also be manufactured using a common method and material for manufacturing an organic light-emitting device.
上述化合物在制造有机发光器件时不仅可以利用真空蒸镀法,还可以利用溶液涂布法来形成有机物层。在这里,所谓溶液涂布法是指旋涂法、浸涂法、喷墨印刷法、丝网印刷法、喷雾法、辊涂法等,但不仅限于此。The above compounds can be used to form an organic layer by vacuum evaporation or solution coating when manufacturing an organic light-emitting device. Here, the so-called solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roller coating, etc., but is not limited to these.
本说明书的有机发光器件的有机物层可以由单层结构形成,也可以由层叠有2层以上的有机物层的多层结构形成。例如,本发明的有机发光器件可以具有包括空穴传输层、空穴注入层、电子阻挡层、空穴传输和注入层、电子传输层、电子注入层、空穴阻挡层、以及电子注入和传输层中的1层以上作为有机物层的结构。但是,本说明书的有机发光器件的结构并不限定于此,可以包括更少数量或更多数量的有机物层。The organic layer of the organic light-emitting device of the present specification may be formed by a single-layer structure or a multi-layer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including a hole transport layer, a hole injection layer, an electron blocking layer, a hole transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and one or more of the electron injection and transport layers as organic layers. However, the structure of the organic light-emitting device of the present specification is not limited thereto and may include a smaller number or a larger number of organic layers.
在本说明书的有机发光器件中,上述有机物层包括空穴注入层、空穴传输层、或者空穴注入和传输层,上述空穴注入层、空穴传输层、或者空穴注入和传输层可以包含由上述的化学式1表示的化合物。In the organic light-emitting device of the present specification, the organic layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer may contain the compound represented by the above Chemical Formula 1.
在本说明书的有机发光器件中,上述有机物层包括空穴传输层或空穴注入层,上述空穴传输层或空穴注入层可以包含由上述的化学式1表示的化合物。In the organic light-emitting device of the present specification, the organic layer includes a hole transport layer or a hole injection layer, and the hole transport layer or the hole injection layer may include the compound represented by the above Chemical Formula 1.
在本说明书的一实施方式中,上述有机物层包括电子阻挡层,上述电子阻挡层包含由上述化学式1表示的化合物。In one embodiment of the present specification, the organic layer includes an electron blocking layer, and the electron blocking layer includes the compound represented by Chemical Formula 1.
在本说明书的一实施方式中,上述有机物层包括电子注入层、电子传输层、电子传输和注入层、或者空穴阻挡层,上述电子注入层、电子传输层、电子传输和注入层、或者空穴阻挡层可以包含由上述的化学式1表示的化合物。In one embodiment of the present specification, the organic layer includes an electron injection layer, an electron transport layer, an electron transport and injection layer, or a hole blocking layer, and the electron injection layer, the electron transport layer, the electron transport and injection layer, or the hole blocking layer may contain the compound represented by the above-mentioned Chemical Formula 1.
在本说明书的有机发光器件中,上述有机物层包括电子传输层、电子注入层、或者电子传输和注入层,上述电子传输层、电子注入层、或者电子传输和注入层可以包含由上述的化学式1表示的化合物。In the organic light-emitting device of the present specification, the organic layer includes an electron transport layer, an electron injection layer, or an electron transport and injection layer, and the electron transport layer, the electron injection layer, or the electron transport and injection layer may contain the compound represented by the above Chemical Formula 1.
在本说明书的一实施方式中,上述有机物层包括电子调节层,上述电子调节层可以包含由上述的化学式1表示的化合物。In one embodiment of the present specification, the organic layer includes an electron adjustment layer, and the electron adjustment layer may include the compound represented by the above Chemical Formula 1.
在本说明书的一实施方式中,上述有机物层包括空穴阻挡层,上述空穴阻挡层包含由上述化学式1表示的化合物。In one embodiment of the present specification, the organic layer includes a hole blocking layer, and the hole blocking layer includes the compound represented by Chemical Formula 1.
在本说明书的有机发光器件中,上述有机物层为电子传输和注入层,上述电子传输和注入层包含由上述的化学式1表示的化合物。In the organic light-emitting device of the present specification, the organic layer is an electron transport and injection layer, and the electron transport and injection layer includes the compound represented by the above Chemical Formula 1.
在本说明书的一实施方式中,包含上述化学式1的化合物的有机物层的厚度为至优选为至更优选为至 In one embodiment of the present specification, the thickness of the organic layer containing the compound of the above Chemical Formula 1 is to Preferably to More preferably to
在本说明书的一实施方式中,上述有机物层包括发光层,上述发光层包含由上述的化学式1表示的化合物。In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound represented by the above Chemical Formula 1.
在本说明书的一实施方式中,上述有机物层包括发光层,上述发光层包含由上述的化学式1表示的化合物作为主体。In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound represented by the above Chemical Formula 1 as a main component.
在本说明书的一实施方式中,上述有机物层包括发光层,上述发光层包含由上述的化学式1表示的化合物作为掺杂剂。In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound represented by the above Chemical Formula 1 as a dopant.
在另一实施方式中,上述有机物层还可以包含除了由上述的化学式1表示的化合物以外的其它有机化合物、金属或金属化合物。In another embodiment, the organic layer may further include other organic compounds, metals or metal compounds in addition to the compound represented by Chemical Formula 1.
在根据本说明书的一实施方式的有机发光器件中,上述发光层还包含荧光掺杂剂或磷光掺杂剂。这时,相对于主体100重量份,发光层内的掺杂剂包含1重量份至50重量份。In the organic light-emitting device according to one embodiment of the present specification, the light-emitting layer further includes a fluorescent dopant or a phosphorescent dopant. In this case, the dopant in the light-emitting layer includes 1 part by weight to 50 parts by weight relative to 100 parts by weight of the host.
作为另一个例子,上述有机物层包括发光层,上述发光层包含由上述化学式1表示的化合物作为主体,还可以包含另外的主体。As another example, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound represented by the chemical formula 1 as a host, and may further include another host.
在本说明书的一实施方式中,上述有机物层包括发光层,上述发光层包含蒽系化合物。In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes an anthracene compound.
在本说明书的一实施方式中,上述有机物层包括发光层,上述发光层包含蒽系化合物作为主体。In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer contains an anthracene compound as a main component.
在本说明书的一实施方式中,上述有机物层包括发光层,上述发光层包含蒽系化合物作为主体,并且还包含掺杂剂。In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes an anthracene-based compound as a host and further includes a dopant.
在本说明书的一实施方式中,上述掺杂剂包含芳基胺系化合物、包含硼和氮的杂环化合物、或者Ir配合物等。In one embodiment of the present specification, the dopant includes an arylamine compound, a heterocyclic compound containing boron and nitrogen, or an Ir complex.
在本说明书的一实施方式中,上述有机物层包括发光层,上述发光层包含蒽系化合物作为主体,包含芳基胺系化合物作为掺杂剂。In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes an anthracene compound as a host and an arylamine compound as a dopant.
在本说明书的一实施方式中,本说明书的有机发光器件还可以包括空穴传输层、空穴注入层、电子阻挡层、电子注入和传输层、电子传输层、电子注入层、空穴阻挡层、以及空穴传输和注入层中的1层以上的有机物层。In one embodiment of the present specification, the organic light-emitting device of the present specification may also include a hole transport layer, a hole injection layer, an electron blocking layer, an electron injection and transport layer, an electron transport layer, an electron injection layer, a hole blocking layer, and one or more organic layers in the hole transport and injection layer.
在本说明书的一实施方式中,上述有机发光器件包括:阳极、阴极、以及设置在上述阳极与上述阴极之间的2层以上的有机物层,上述2层以上的有机物层中的至少一层包含由上述化学式1表示的化合物。In one embodiment of the present specification, the organic light-emitting device includes: an anode, a cathode, and two or more organic layers arranged between the anode and the cathode, and at least one of the two or more organic layers contains the compound represented by the above Chemical Formula 1.
在本说明书的一实施方式中,上述2层以上的有机物层可以从由发光层、空穴传输层、空穴注入层、空穴传输和注入层、以及电子阻挡层组成的组中选择二者以上。In one embodiment of the present specification, the two or more organic layers may be two or more selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, a hole transport and injection layer, and an electron blocking layer.
在本说明书的一实施方式中,上述2层以上的有机物层可以从由发光层、电子传输层、电子注入层、电子传输和注入层、电子调节层、以及空穴阻挡层组成的组中选择二者以上。In one embodiment of the present specification, the two or more organic layers may be selected from the group consisting of a light emitting layer, an electron transport layer, an electron injection layer, an electron transport and injection layer, an electron regulating layer, and a hole blocking layer.
在本说明书的一实施方式中,上述有机物层包括2层以上的电子传输层,上述2层以上的电子传输层中的至少一层包含由上述化学式1表示的化合物。具体而言,在本说明书的一实施方式中,由上述化学式1表示的化合物可以包含在上述2层以上的电子传输层中的1层中,也可以包含在2层以上的电子传输层的各层中。In one embodiment of the present specification, the organic layer includes two or more electron transport layers, and at least one of the two or more electron transport layers contains the compound represented by the chemical formula 1. Specifically, in one embodiment of the present specification, the compound represented by the chemical formula 1 may be contained in one of the two or more electron transport layers, or may be contained in each of the two or more electron transport layers.
另外,在本说明书的一实施方式中,上述化合物包含在上述2层以上的电子传输层的各层中时,除了由上述化学式1表示的化合物以外的其它材料可以彼此相同或不同。In one embodiment of the present specification, when the compound is included in each of the two or more electron transport layers, materials other than the compound represented by the chemical formula 1 may be the same as or different from each other.
包含由上述化学式1表示的化合物的有机物层为电子传输层、电子注入层、或者电子传输和注入层时,上述电子传输层、电子注入层、或者电子传输和注入层还可以包含n型掺杂剂。上述n型掺杂剂可以使用本技术领域中已知的材料,例如,可以使用金属或金属配合物。例如,包含由上述化学式1表示的化合物的电子传输层还可以包含LiQ(LithiumQuinolate,喹啉锂)。根据一个例子,可以以2:8至8:2,例如4:6至6:4的重量比包含由上述化学式1表示的化合物和上述n型掺杂剂。When the organic layer containing the compound represented by the above chemical formula 1 is an electron transport layer, an electron injection layer, or an electron transport and injection layer, the above electron transport layer, the electron injection layer, or the electron transport and injection layer may further include an n-type dopant. The above n-type dopant may use materials known in the art, for example, a metal or a metal complex may be used. For example, the electron transport layer containing the compound represented by the above chemical formula 1 may further include LiQ (LithiumQuinolate, quinoline lithium). According to an example, the compound represented by the above chemical formula 1 and the above n-type dopant may be included in a weight ratio of 2:8 to 8:2, for example, 4:6 to 6:4.
根据一个例子,可以以1:1的重量比包含由上述化学式1表示的化合物和上述n型掺杂剂。According to an example, the compound represented by the above Chemical Formula 1 and the above n-type dopant may be included in a weight ratio of 1:1.
在本说明书的一实施方式中,上述有机物层包括2层以上的空穴传输层,上述2层以上的空穴传输层中的至少一层包含由上述化学式1表示的化合物。具体而言,在本说明书的一实施方式中,由上述化学式1表示的化合物可以包含在上述2层以上的空穴传输层中的1层中,也可以包含在2层以上的空穴传输层的各层中。In one embodiment of the present specification, the organic layer includes two or more hole transport layers, and at least one of the two or more hole transport layers contains the compound represented by the chemical formula 1. Specifically, in one embodiment of the present specification, the compound represented by the chemical formula 1 may be contained in one of the two or more hole transport layers, or may be contained in each of the two or more hole transport layers.
另外,在本说明书的一实施方式中,由上述化学式1表示的化合物包含在上述2层以上的空穴传输层的各层中时,除了由上述化学式1表示的化合物以外的其它材料可以彼此相同或不同。In one embodiment of the present specification, when the compound represented by the above Chemical Formula 1 is included in each of the two or more hole transport layers, materials other than the compound represented by the above Chemical Formula 1 may be the same as or different from each other.
在本说明书的一实施方式中,上述有机物层除了包括包含由上述化学式1表示的化合物的有机物层以外,还可以包括空穴注入层或空穴传输层,该空穴注入层或空穴传输层包含含有芳基胺基、咔唑基或苯并咔唑基的化合物。In one embodiment of the present specification, the organic layer may include a hole injection layer or a hole transport layer in addition to the organic layer including the compound represented by the above Chemical Formula 1, wherein the hole injection layer or the hole transport layer includes a compound containing an arylamine group, a carbazole group or a benzocarbazole group.
在本说明书的一实施方式中,上述有机发光器件可以是在基板上依次层叠有阳极、1层以上的有机物层和阴极的结构(正常型(normal type))的有机发光器件。In one embodiment of the present specification, the organic light-emitting device may be a (normal type) organic light-emitting device having a structure in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.
在本说明书的一实施方式中,上述有机发光器件可以是在基板上依次层叠有阴极、1层以上的有机物层和阳极的逆向结构(倒置型(inverted type))的有机发光器件。In one embodiment of the present specification, the organic light emitting device may be an organic light emitting device of a reverse structure (inverted type) in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.
在本发明的有机发光器件中,上述有机物层可以包括电子阻挡层,上述电子阻挡层可以使用本技术领域中已知的材料。In the organic light-emitting device of the present invention, the organic layer may include an electron blocking layer, and the electron blocking layer may be made of materials known in the technical field.
例如,上述有机发光器件可以具有如下所示的层叠结构,但不仅限于此。For example, the organic light emitting device may have a stacked structure as shown below, but is not limited thereto.
(1)阳极/空穴传输层/发光层/阴极(1) Anode/hole transport layer/light-emitting layer/cathode
(2)阳极/空穴注入层/空穴传输层/发光层/阴极(2) Anode/hole injection layer/hole transport layer/light-emitting layer/cathode
(3)阳极/空穴注入层/空穴缓冲层/空穴传输层/发光层/阴极(3) Anode/hole injection layer/hole buffer layer/hole transport layer/light-emitting layer/cathode
(4)阳极/空穴传输层/发光层/电子传输层/阴极(4) Anode/hole transport layer/light-emitting layer/electron transport layer/cathode
(5)阳极/空穴传输层/发光层/电子传输层/电子注入层/阴极(5) Anode/hole transport layer/light-emitting layer/electron transport layer/electron injection layer/cathode
(6)阳极/空穴注入层/空穴传输层/发光层/电子传输层/阴极(6) Anode/hole injection layer/hole transport layer/light-emitting layer/electron transport layer/cathode
(7)阳极/空穴注入层/空穴传输层/发光层/电子传输层/电子注入层/阴极(7) Anode/hole injection layer/hole transport layer/light-emitting layer/electron transport layer/electron injection layer/cathode
(8)阳极/空穴注入层/空穴缓冲层/空穴传输层/发光层/电子传输层/阴极(8) Anode/hole injection layer/hole buffer layer/hole transport layer/light-emitting layer/electron transport layer/cathode
(9)阳极/空穴注入层/空穴缓冲层/空穴传输层/发光层/电子传输层/电子注入层/阴极(9) Anode/hole injection layer/hole buffer layer/hole transport layer/light-emitting layer/electron transport layer/electron injection layer/cathode
(10)阳极/空穴传输层/电子阻挡层/发光层/电子传输层/阴极(10) Anode/hole transport layer/electron blocking layer/light-emitting layer/electron transport layer/cathode
(11)阳极/空穴传输层/电子阻挡层/发光层/电子传输层/电子注入层/阴极(11) Anode/hole transport layer/electron blocking layer/light-emitting layer/electron transport layer/electron injection layer/cathode
(12)阳极/空穴注入层/空穴传输层/电子阻挡层/发光层/电子传输层/阴极(12) Anode/hole injection layer/hole transport layer/electron blocking layer/light-emitting layer/electron transport layer/cathode
(13)阳极/空穴注入层/空穴传输层/电子阻挡层/发光层/电子传输层/电子注入层/阴极(13) Anode/hole injection layer/hole transport layer/electron blocking layer/light-emitting layer/electron transport layer/electron injection layer/cathode
(14)阳极/空穴传输层/发光层/空穴阻挡层/电子传输层/阴极(14) Anode/hole transport layer/light-emitting layer/hole blocking layer/electron transport layer/cathode
(15)阳极/空穴传输层/发光层/空穴阻挡层/电子传输层/电子注入层/阴极(15) Anode/hole transport layer/light-emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode
(16)阳极/空穴注入层/空穴传输层/发光层/空穴阻挡层/电子传输层/阴极(16) Anode/hole injection layer/hole transport layer/light-emitting layer/hole blocking layer/electron transport layer/cathode
(17)阳极/空穴注入层/空穴传输层/发光层/空穴阻挡层/电子传输层/电子注入层/阴极(17) Anode/hole injection layer/hole transport layer/light-emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode
本说明书的有机发光器件的结构可以具有如图1和图2所示的结构,但不仅限于此。The structure of the organic light-emitting device of the present specification may have the structure shown in FIG. 1 and FIG. 2 , but is not limited thereto.
图1例示了依次层叠有基板1、阳极2、有机物层10和阴极9的有机发光器件的结构。在如上所述的结构中,上述化合物可以包含在上述有机物层10中。1 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, an organic layer 10, and a cathode 9 are sequentially stacked. In the above structure, the above compound may be contained in the above organic layer 10.
图2例示了依次层叠有基板1、阳极2、空穴注入层3、空穴传输层4、电子阻挡层5、发光层6、空穴阻挡层7、电子注入和传输层8、以及阴极9的有机发光器件的结构。在如上所述的结构中,上述化合物可以包含在空穴注入层3、空穴传输层4、电子阻挡层5、发光层6、空穴阻挡层7、或者电子注入和传输层8中。2 illustrates a structure of an organic light-emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, a hole blocking layer 7, an electron injection and transport layer 8, and a cathode 9 are sequentially stacked. In the structure described above, the above-mentioned compound may be contained in the hole injection layer 3, the hole transport layer 4, the electron blocking layer 5, the light-emitting layer 6, the hole blocking layer 7, or the electron injection and transport layer 8.
在本说明书的一实施方式中,上述电子阻挡层和发光层可以相邻设置。例如,上述电子阻挡层和发光层可以物理相接而设置。In one embodiment of the present specification, the electron blocking layer and the light emitting layer may be disposed adjacent to each other. For example, the electron blocking layer and the light emitting layer may be disposed in physical contact with each other.
在本说明书的一实施方式中,上述空穴传输层和电子阻挡层可以相邻设置。例如,上述空穴传输层和电子阻挡层可以物理相接而设置。In one embodiment of the present specification, the hole transport layer and the electron blocking layer may be disposed adjacent to each other. For example, the hole transport layer and the electron blocking layer may be disposed in physical contact with each other.
本说明书的有机发光器件除了有机物层中的1层以上包含上述化合物,即由上述化学式1表示的化合物以外,可以利用本技术领域中已知的材料和方法进行制造。The organic light-emitting device of the present specification can be manufactured using materials and methods known in the technical field, except that at least one layer of the organic material layer contains the above compound, that is, the compound represented by the above Chemical Formula 1.
上述有机发光器件包括复数个有机物层时,上述有机物层可以由相同的物质或不同的物质形成。When the organic light-emitting device includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.
例如,根据本说明书的有机发光器件可以如下进行制造:利用溅射(sputtering)或电子束蒸发(e-beam evaporation)之类的PVD(physical vapor deposition:物理气相沉积)方法,在基板上蒸镀金属或具有导电性的金属氧化物或它们的合金而形成阳极,然后在该阳极上形成包括空穴注入层、空穴传输层、发光层、电子阻挡层、电子传输层和电子注入层的有机物层,之后在该有机物层上蒸镀可用作阴极的物质而制造。除了这种方法以外,也可以在基板上依次蒸镀阴极物质、有机物层、阳极物质而制造有机发光器件。For example, the organic light-emitting device according to the present specification can be manufactured as follows: using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, a metal or a conductive metal oxide or an alloy thereof is evaporated on a substrate to form an anode, and then an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, an electron blocking layer, an electron transport layer and an electron injection layer is formed on the anode, and then a substance that can be used as a cathode is evaporated on the organic layer. In addition to this method, an organic light-emitting device can also be manufactured by sequentially evaporating a cathode substance, an organic layer, and an anode substance on a substrate.
上述有机物层还可以包括空穴传输层、空穴注入层、电子阻挡层、电子注入和传输层、电子传输层、电子注入层、空穴阻挡层、以及空穴传输和注入层中的一层以上。The organic layer may further include one or more of a hole transport layer, a hole injection layer, an electron blocking layer, an electron injection and transport layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole transport and injection layer.
上述有机物层可以为包括空穴注入层、空穴传输层、电子注入和传输层、电子阻挡层、发光层和电子传输层、电子注入层、电子注入和传输层等的多层结构,但并不限定于此,也可以为单层结构。此外,上述有机物层可以使用各种高分子材料并通过不是蒸镀法的溶剂工序(solvent process),例如旋涂法、浸涂法、刮涂法、丝网印刷法、喷墨印刷法、或者热转印法等方法来制造成更少数量的层。The organic layer may be a multilayer structure including a hole injection layer, a hole transport layer, an electron injection and transport layer, an electron blocking layer, a light emitting layer and an electron transport layer, an electron injection layer, an electron injection and transport layer, but is not limited thereto and may also be a single layer structure. In addition, the organic layer may be made of various polymer materials and by a solvent process other than evaporation, such as spin coating, dip coating, blade coating, screen printing, inkjet printing, or thermal transfer to form a smaller number of layers.
上述阳极是注入空穴的电极,作为阳极物质,通常为了使空穴能够顺利地向有机物层注入,优选为功函数大的物质。作为本发明中可以使用的阳极物质的具体的例子,有钒、铬、铜、锌、金等金属或它们的合金;氧化锌、氧化铟、氧化铟锡(ITO,Indium TinOxide)、氧化铟锌(IZO,Indium Zinc Oxide)等金属氧化物;ZnO:Al或SnO2:Sb等金属与氧化物的组合;聚(3-甲基噻吩)、聚[3,4-(亚乙基-1,2-二氧)噻吩](PEDOT)、聚吡咯和聚苯胺等导电性高分子等,但不仅限于此。The anode is an electrode for injecting holes. As the anode material, in order to smoothly inject holes into the organic layer, a material with a large work function is preferably used. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO, Indium Tin Oxide), indium zinc oxide (IZO, Indium Zinc Oxide); combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.
上述阴极是注入电子的电极,作为阴极物质,通常为了使电子容易地向有机物层注入,优选为功函数小的物质。作为阴极物质的具体的例子,有镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡和铅等金属或它们的合金;LiF/Al或LiO2/Al等多层结构物质等,但不仅限于此。The cathode is an electrode for injecting electrons. In order to facilitate the injection of electrons into the organic layer, the cathode material is preferably a material with a small work function. Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; multilayer structure materials such as LiF/Al or LiO2 /Al, etc., but are not limited thereto.
上述空穴注入层是起到使从阳极到发光层的空穴的注入顺利的作用的层,空穴注入物质是可以在低电压下从阳极良好地接收空穴的物质,优选空穴注入物质的HOMO(最高占有分子轨道,highest occupied molecular orbital)介于阳极物质的功函数与周围有机物层的HOMO之间。作为空穴注入物质的具体的例子,有金属卟啉(porphyrine)、低聚噻吩、芳基胺系有机物、六腈六氮杂苯并菲系有机物、喹吖啶酮(quinacridone)系有机物、苝(perylene)系有机物、蒽醌及聚苯胺和聚噻吩系的导电性高分子等,但不仅限于此。空穴注入层的厚度可以为1至150nm。当上述空穴注入层的厚度为1nm以上时,具有可以防止空穴注入特性降低的优点,当150nm以下时,具有可以防止空穴注入层的厚度太厚时为了提高空穴的迁移而驱动电压上升的优点。The hole injection layer is a layer that plays a role in making the injection of holes from the anode to the light-emitting layer smooth. The hole injection material is a material that can receive holes well from the anode at a low voltage. The HOMO (highest occupied molecular orbital) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic layer. As specific examples of hole injection materials, there are metal porphyrines, oligothiophenes, arylamine organics, hexanitrile hexaazatriphenylene organics, quinacridone organics, perylene organics, anthraquinone and polyaniline and polythiophene conductive polymers, but are not limited to this. The thickness of the hole injection layer can be 1 to 150nm. When the thickness of the hole injection layer is more than 1nm, it has the advantage of preventing the hole injection characteristics from being reduced. When it is less than 150nm, it has the advantage of preventing the driving voltage from rising when the thickness of the hole injection layer is too thick in order to improve the migration of holes.
上述空穴传输层可以起到使空穴的传输顺利的作用。空穴传输物质是能够从阳极或空穴注入层接收空穴并将其转移至发光层的物质,对空穴的迁移率大的物质是合适的。作为具体的例子,有芳基胺系有机物、导电性高分子、以及同时存在共轭部分和非共轭部分的嵌段共聚物等,但不仅限于此。The hole transport layer can play a role in making the hole transport smooth. The hole transport material is a material that can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer, and a material with a large hole mobility is suitable. As specific examples, there are aromatic amine organic substances, conductive polymers, and block copolymers with both conjugated parts and non-conjugated parts, but are not limited to these.
在空穴注入层与空穴传输层之间可以进一步设置空穴缓冲层,可以包含本技术领域中已知的空穴注入或传输的材料。A hole buffer layer may be further disposed between the hole injection layer and the hole transport layer, and may include hole injection or transport materials known in the art.
在空穴传输层与发光层之间可以设置电子阻挡层。在上述电子阻挡层中可以使用上述的化合物或本技术领域中已知的材料。An electron blocking layer may be provided between the hole transport layer and the light emitting layer. The electron blocking layer may be made of the above-mentioned compounds or materials known in the art.
上述发光层可以发出红色、绿色或蓝色的光,可以由磷光物质或荧光物质形成。上述发光物质是能够从空穴传输层和电子传输层分别接收空穴和电子并使它们结合而发出可见光区域的光的物质,优选为对于荧光或磷光的量子效率高的物质。作为具体的例子,有8-羟基-喹啉铝配合物(Alq3);咔唑系化合物;二聚苯乙烯基(dimerized styryl)化合物;BAlq;10-羟基苯并喹啉-金属化合物;苯并唑、苯并噻唑及苯并咪唑系化合物;聚(对亚苯基亚乙烯基)(PPV)系高分子;螺环(spiro)化合物;聚芴、红荧烯等,但不仅限于此。The light-emitting layer can emit red, green or blue light and can be formed of a phosphorescent material or a fluorescent material. The light-emitting material is a material that can receive holes and electrons from the hole transport layer and the electron transport layer respectively and combine them to emit light in the visible light region, and is preferably a material with high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); carbazole compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo azole, benzothiazole and benzimidazole compounds; poly(p-phenylene vinylene) (PPV) polymers; spiro compounds; polyfluorene, rubrene, etc., but are not limited to these.
作为发光层的主体材料,有芳香族稠环衍生物或含杂环化合物等。具体而言,作为芳香族稠环衍生物,有蒽衍生物、芘衍生物、萘衍生物、并五苯衍生物、菲化合物、荧蒽化合物等,作为含杂环化合物,有咔唑衍生物、二苯并呋喃衍生物、梯型呋喃化合物嘧啶衍生物等,但并不限定于此。The main material of the light-emitting layer includes aromatic fused ring derivatives or heterocyclic compounds. Specifically, aromatic fused ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, etc. Pyrimidine derivatives, etc., but are not limited thereto.
当发光层发出红色光时,作为发光掺杂剂,可以使用PIQIr(acac)(bi s(1-phenylisoquinoline)acetylacetonateiridium,双(1-苯基异喹啉)乙酰丙酮合铱)、PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium,双(1-苯基喹啉)乙酰丙酮合铱)、PQIr(tris(1-phenylquinoline)iridium,三(1-苯基喹啉)合铱)、PtOEP(octaethylporphyrin platinum,铂八乙基卟啉)等磷光物质,或Alq3(tris(8-hydroxyquinolino)aluminum,三(8-羟基喹啉)铝)等荧光物质,但不仅限于此。当发光层发出绿色光时,作为发光掺杂剂,可以使用Ir(ppy)3(fac tris(2-phenylpyridine)iridium,面式三(2-苯基吡啶)合铱)等磷光物质、或Alq3(三(8-羟基喹啉)铝)等荧光物质,但不仅限于此。当发光层发出蓝色光时,作为发光掺杂剂,可以使用(4,6-F2ppy)2Irpic等磷光物质,或螺-DPVBi(spiro-DPVBi)、螺-6P(spiro-6P)、二苯乙烯基苯(DS B)、二苯乙烯基亚芳基(DSA)、PFO系高分子、PPV系高分子等荧光物质,但不仅限于此。When the light-emitting layer emits red light, as a light-emitting dopant, phosphorescent substances such as PIQIr(acac) (bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac) (bis(1-phenylquinoline)acetylacetonateiridium), PQIr(tris(1-phenylquinoline)iridium), PtOEP (octaethylporphyrin platinum), or fluorescent substances such as Alq3 (tris(8-hydroxyquinolino)aluminum), can be used, but are not limited to these. When the light-emitting layer emits green light, as a light-emitting dopant, phosphorescent materials such as Ir(ppy) 3 (fac tris(2-phenylpyridine)iridium, face tris(2-phenylpyridine)iridium) or fluorescent materials such as Alq 3 (tris(8-hydroxyquinoline)aluminum) can be used, but the invention is not limited thereto. When the light-emitting layer emits blue light, as a light-emitting dopant, phosphorescent materials such as (4,6-F 2 ppy) 2 Irpic or fluorescent materials such as spiro-DPVBi, spiro-6P, distyrylbenzene (DSB), distyrylaryl (DSA), PFO-based polymers, and PPV-based polymers can be used, but the invention is not limited thereto.
在电子传输层与发光层之间可以设置空穴阻挡层,可以使用本技术领域中已知的材料。A hole blocking layer may be provided between the electron transport layer and the light emitting layer, and a material known in the technical field may be used.
上述电子传输层可以起到使电子的传输顺利的作用。电子传输物质是可以从阴极良好地接收电子并将其转移至发光层的物质,对电子的迁移率大的物质是合适的。作为具体的例子,有上面提到的化合物或8-羟基喹啉的Al配合物、包含Alq3的配合物、有机自由基化合物、羟基黄酮-金属配合物等,但不仅限于此。电子传输层的厚度可以为1至50nm。当电子传输层的厚度为1nm以上时,具有可以防止电子传输特性降低的优点,当50nm以下时,具有可以防止电子传输层的厚度太厚时为了提高电子的迁移而驱动电压上升的优点。The above-mentioned electron transport layer can play a role in making the transmission of electrons smooth. The electron transport material is a material that can receive electrons well from the cathode and transfer them to the light-emitting layer, and is suitable for materials with high electron mobility. As specific examples, there are the above-mentioned compounds or Al complexes of 8-hydroxyquinoline, complexes containing Alq 3 , organic free radical compounds, hydroxyflavone-metal complexes, etc., but are not limited to this. The thickness of the electron transport layer can be 1 to 50nm. When the thickness of the electron transport layer is more than 1nm, it has the advantage of preventing the electron transport characteristics from being reduced. When it is less than 50nm, it has the advantage of preventing the driving voltage from rising in order to improve the migration of electrons when the thickness of the electron transport layer is too thick.
上述电子注入层可以起到使电子的注入顺利的作用。作为电子注入物质,优选为如下化合物:具有传输电子的能力,具有注入来自阴极的电子的效果,具有对于发光层或发光材料的优异的电子注入效果,防止发光层中所生成的激子向空穴注入层迁移,而且薄膜形成能力优异的化合物。具体而言,有芴酮、蒽醌二甲烷、联苯醌、噻喃二氧化物、唑、二唑、三唑、咪唑、苝四羧酸、亚芴基甲烷、蒽酮等和它们的衍生物、金属配位化合物、以及含氮五元环衍生物等,但并不限定于此。The electron injection layer can play a role in facilitating the injection of electrons. As the electron injection material, the following compounds are preferred: compounds that have the ability to transport electrons, have the effect of injecting electrons from the cathode, have an excellent electron injection effect on the light-emitting layer or the light-emitting material, prevent the excitons generated in the light-emitting layer from migrating to the hole injection layer, and have excellent thin film forming ability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Examples include, but are not limited to, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylene methane, anthrone, and derivatives thereof, metal coordination compounds, and nitrogen-containing five-membered ring derivatives.
作为上述金属配位化合物,有8-羟基喹啉锂、双(8-羟基喹啉)锌、双(8-羟基喹啉)铜、双(8-羟基喹啉)锰、三(8-羟基喹啉)铝、三(2-甲基-8-羟基喹啉)铝、三(8-羟基喹啉)镓、双(10-羟基苯并[h]喹啉)铍、双(10-羟基苯并[h]喹啉)锌、双(2-甲基-8-喹啉)氯化镓、双(2-甲基-8-喹啉)(邻甲酚)镓、双(2-甲基-8-喹啉)(1-萘酚)铝、双(2-甲基-8-喹啉)(2-萘酚)镓等,但并不限定于此。Examples of the metal coordination compounds include, but are not limited to, 8-hydroxyquinoline lithium, bis(8-hydroxyquinoline) zinc, bis(8-hydroxyquinoline) copper, bis(8-hydroxyquinoline) manganese, tris(8-hydroxyquinoline) aluminum, tris(2-methyl-8-hydroxyquinoline) aluminum, tris(8-hydroxyquinoline) gallium, bis(10-hydroxybenzo[h]quinoline) beryllium, bis(10-hydroxybenzo[h]quinoline) zinc, bis(2-methyl-8-quinoline) gallium chloride, bis(2-methyl-8-quinoline)(o-cresol) gallium, bis(2-methyl-8-quinoline)(1-naphthol) aluminum, and bis(2-methyl-8-quinoline)(2-naphthol) gallium.
上述空穴阻挡层是阻止空穴到达阴极的层,通常可以利用与空穴注入层相同的条件形成。具体而言,有二唑衍生物或三唑衍生物、菲咯啉衍生物、BCP、铝配合物(aluminum complex)等,但并不限定于此。The hole blocking layer is a layer that prevents holes from reaching the cathode and can usually be formed using the same conditions as the hole injection layer. Examples of the compound include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, and aluminum complexes.
根据所使用的材料,根据本发明的有机发光器件可以为顶部发光型、底部发光型或双向发光型。The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type according to the materials used.
下面,为了对本说明书具体地进行说明,将举出实施例详细地进行说明。但是,根据本说明书的实施例可以变形为各种不同的形态,不解释为本申请的范围限定于下文中详述的实施例。本申请的实施例是为了向本领域技术人员更完整地说明本说明书而提供的。Below, in order to specifically describe this specification, an embodiment will be cited to describe in detail. However, the embodiments according to this specification can be deformed into various different forms, and it is not interpreted that the scope of this application is limited to the embodiments described in detail below. The embodiments of this application are provided to more completely describe this specification to those skilled in the art.
<合成例><Synthesis Example>
合成例1.化合物1的合成Synthesis Example 1. Synthesis of Compound 1
在N-([1,1',4',1”-三联苯]-4-基)-9,9-二甲基-9H-芴-2-胺(20.0g,45.70mmol)和6-溴-7-甲基-1,2,3,4-四氢萘(10.50g,46.62mmol)、以及叔丁醇钠(5.41g,56.27mmol)中加入甲苯(300ml)后,加热搅拌10分钟。在上述混合物中,加入溶解于甲苯(30ml)的双(三叔丁基膦)钯(0.10g,0.20mmol)后,加热搅拌1小时。反应结束及过滤后,用甲苯和水进行层分离。去除溶剂后,用乙酸乙酯重结晶,从而获得了上述化合物1(20.0g,75.22%收率)。(MS[M+H]+=582)Toluene (300 ml) was added to N-([1,1',4',1"-terphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (20.0 g, 45.70 mmol), 6-bromo-7-methyl-1,2,3,4-tetrahydronaphthalene (10.50 g, 46.62 mmol), and sodium tert-butoxide (5.41 g, 56.27 mmol), followed by heating and stirring for 10 minutes. Bis(tri-tert-butylphosphine)palladium (0.10 g, 0.20 mmol) dissolved in toluene (30 ml) was added to the above mixture, followed by heating and stirring for 1 hour. After the reaction was completed and filtered, the layers were separated with toluene and water. After removing the solvent, the mixture was recrystallized with ethyl acetate to obtain the above compound 1 (20.0 g, 75.22% yield). (MS[M+H] + =582)
合成例2.化合物2的合成Synthesis Example 2. Synthesis of Compound 2
利用9,9-二甲基-3-苯-9H-芴-2-胺(10.0g,35.04mmol)和6-溴-7-异丙基-1,2,3,4-四氢萘(9.05g,35.74mmol),通过与上述合成例1相同的方法获得了上述化合物2(17.5g,79.28%收率)。(MS[M+H]+=630)Using 9,9-dimethyl-3-phenyl-9H-fluorene-2-amine (10.0 g, 35.04 mmol) and 6-bromo-7-isopropyl-1,2,3,4-tetrahydronaphthalene (9.05 g, 35.74 mmol), the above-mentioned compound 2 (17.5 g, 79.28% yield) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS[M+H] + =630)
合成例3.化合物3的合成Synthesis Example 3. Synthesis of Compound 3
利用N-([1,1'-联苯]-4-基)-9,9-二甲基-3-苯-9H-芴-2-胺(20.0g,45.70mmol)和6-溴-1,1,4,4,7-五甲基-1,2,3,4-四氢萘(13.12g,46.62mmol),通过与上述合成例1相同的方法获得了上述化合物3(22.0g,75.47%收率)。(MS[M+H]+=638)Using N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-3-phenyl-9H-fluoren-2-amine (20.0 g, 45.70 mmol) and 6-bromo-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene (13.12 g, 46.62 mmol), the above-mentioned compound 3 (22.0 g, 75.47% yield) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS[M+H] + =638)
合成例4.化合物4的合成Synthesis Example 4. Synthesis of Compound 4
利用9,9-二甲基-N,3-二苯基-9H-芴-2-胺(20.0g,55.33mmol)和6-溴-1,1,4,4-四甲基-7-苯-1,2,3,4-四氢萘(19.37g,56.43mmol),通过与上述合成例1相同的方法获得了上述化合物4(27.0g,78.22%收率)。(MS[M+H]+=624)Using 9,9-dimethyl-N,3-diphenyl-9H-fluoren-2-amine (20.0 g, 55.33 mmol) and 6-bromo-1,1,4,4-tetramethyl-7-benzene-1,2,3,4-tetrahydronaphthalene (19.37 g, 56.43 mmol), the above-mentioned compound 4 (27.0 g, 78.22% yield) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS[M+H] + =624)
合成例5.化合物5的合成Synthesis Example 5. Synthesis of Compound 5
利用9,9-二甲基-3-苯-9H-芴-2-胺(10.0g,35.04mmol)和6-溴-1,1,4,4,7-五甲基-1,2,3,4-四氢萘(10.05g,35.74mmol),通过与上述合成例1相同的方法获得了上述化合物5(19.0g,79.04%收率)。(MS[M+H]+=686)Using 9,9-dimethyl-3-phenyl-9H-fluorene-2-amine (10.0 g, 35.04 mmol) and 6-bromo-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene (10.05 g, 35.74 mmol), the above-mentioned compound 5 (19.0 g, 79.04% yield) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS [M+H] + = 686)
合成例6.化合物6的合成Synthesis Example 6. Synthesis of Compound 6
利用9,9-二甲基-3-苯-9H-芴-2-胺(10.0g,35.04mmol)和5-溴-1,1,4,4,6-五甲基-1,2,3,4-四氢萘(10.05g,35.74mmol),通过与上述合成例1相同的方法获得了上述化合物6(18.5g,76.96%收率)。(MS[M+H]+=686)Using 9,9-dimethyl-3-phenyl-9H-fluorene-2-amine (10.0 g, 35.04 mmol) and 5-bromo-1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (10.05 g, 35.74 mmol), the above-mentioned compound 6 (18.5 g, 76.96% yield) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS[M+H] + =686)
合成例7.化合物7的合成Synthesis Example 7. Synthesis of Compound 7
利用3,9,9-三苯基-9H-芴-2-胺(10.0g,24.42mmol)和6-溴-7-异丙基-1,2,3,4-四氢萘(6.31g,24.91mmol),通过与上述合成例1相同的方法获得了上述化合物7(14.5g,78.74%收率)。(MS[M+H]+=754)Using 3,9,9-triphenyl-9H-fluorene-2-amine (10.0 g, 24.42 mmol) and 6-bromo-7-isopropyl-1,2,3,4-tetrahydronaphthalene (6.31 g, 24.91 mmol), the above-mentioned compound 7 (14.5 g, 78.74% yield) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS[M+H] + =754)
合成例8.化合物8的合成Synthesis Example 8. Synthesis of Compound 8
利用N-([1,1'-联苯]-4-基)-3,9,9-三苯基-9H-芴-2-胺(20.0g,35.60mmol)和6-溴-1,1,4,4,7-五甲基-1,2,3,4-四氢萘(10.21g,36.32mmol),通过与上述合成例1相同的方法获得了上述化合物8(21.0g,77.41%收率)。(MS[M+H]+=762)Using N-([1,1'-biphenyl]-4-yl)-3,9,9-triphenyl-9H-fluoren-2-amine (20.0 g, 35.60 mmol) and 6-bromo-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene (10.21 g, 36.32 mmol), the above-mentioned compound 8 (21.0 g, 77.41% yield) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS[M+H] + =762)
合成例9.化合物9的合成Synthesis Example 9. Synthesis of Compound 9
利用N,3,9,9-四苯基-9H-芴-2-胺(20.0g,41.18mmol)和6-溴-1,1,4,4-四甲基-7-苯-1,2,3,4-四氢萘(14.42g,42.01mmol),通过与上述合成例1相同的方法获得了上述化合物9(24.5g,78.54%收率)。(MS[M+H]+=748)Using N,3,9,9-tetraphenyl-9H-fluorene-2-amine (20.0 g, 41.18 mmol) and 6-bromo-1,1,4,4-tetramethyl-7-benzene-1,2,3,4-tetrahydronaphthalene (14.42 g, 42.01 mmol), the above-mentioned compound 9 (24.5 g, 78.54% yield) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS[M+H] + =748)
合成例10.化合物10的合成Synthesis Example 10. Synthesis of Compound 10
利用3,9,9-三苯基-9H-芴-2-胺(10.0g,24.42mmol)和6-溴-1,1,4,4,7-五甲基-1,2,3,4-四氢萘(7.00g,24.91mmol),通过与上述合成例1相同的方法获得了上述化合物10(15.5g,78.34%收率)。(MS[M+H]+=810)Using 3,9,9-triphenyl-9H-fluorene-2-amine (10.0 g, 24.42 mmol) and 6-bromo-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene (7.00 g, 24.91 mmol), the above-mentioned compound 10 (15.5 g, 78.34% yield) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS[M+H] + =810)
合成例11.化合物11的合成Synthesis Example 11. Synthesis of Compound 11
利用3-(萘-1-基)-9,9-二苯基-9H-芴-2-胺(10.0g,21.76mmol)和6-溴-1,1,4,4,7-五甲基-1,2,3,4-四氢萘(6.24g,22.19mmol),通过与上述合成例1相同的方法获得了上述化合物11(14.5g,77.46%)。(MS[M+H]+=860)Using 3-(naphthalen-1-yl)-9,9-diphenyl-9H-fluoren-2-amine (10.0 g, 21.76 mmol) and 6-bromo-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene (6.24 g, 22.19 mmol), the above-mentioned compound 11 (14.5 g, 77.46%) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS[M+H] + =860)
合成例12.化合物12的合成Synthesis Example 12. Synthesis of Compound 12
利用3-(萘-2-基)-9,9-二苯基-9H-芴-2-胺(10.0g,21.76mmol)和6-溴-1,1,4,4,7-五甲基-1,2,3,4-四氢萘(6.24g,22.19mmol),通过与上述合成例1相同的方法获得了上述化合物12(15.0g,80.13%)。(MS[M+H]+=860)Using 3-(naphthalen-2-yl)-9,9-diphenyl-9H-fluoren-2-amine (10.0 g, 21.76 mmol) and 6-bromo-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene (6.24 g, 22.19 mmol), the above-mentioned compound 12 (15.0 g, 80.13%) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS[M+H] + =860)
合成例13.化合物13的合成Synthesis Example 13. Synthesis of Compound 13
利用3-苯-9,9'-螺二[芴]-2-胺(10.0g,24.54mmol)和6-溴-7-甲基-1,2,3,4-四氢萘(5.63g,25.03mmol),通过与上述合成例1相同的方法获得了上述化合物13(13.5g,78.93%收率)。(MS[M+H]+=696)Using 3-benzene-9,9'-spirobi[fluorene]-2-amine (10.0 g, 24.54 mmol) and 6-bromo-7-methyl-1,2,3,4-tetrahydronaphthalene (5.63 g, 25.03 mmol), the above-mentioned compound 13 (13.5 g, 78.93% yield) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS[M+H] + =696)
合成例14.化合物14的合成Synthesis Example 14. Synthesis of Compound 14
利用3-苯-9,9'-螺二[芴]-2-胺(10.0g,24.54mmol)和6-溴-1,1,4,4,7-五甲基-1,2,3,4-四氢萘(7.04g,25.03mmol),通过与上述合成例1相同的方法获得了上述化合物14(15.5g,78.15%收率)。(MS[M+H]+=808)Using 3-benzene-9,9'-spirobi[fluorene]-2-amine (10.0 g, 24.54 mmol) and 6-bromo-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene (7.04 g, 25.03 mmol), the above-mentioned compound 14 (15.5 g, 78.15% yield) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS[M+H] + =808)
<实验例和比较实验例><Experimental Examples and Comparative Experimental Examples>
实验例1-1Experimental Example 1-1
将ITO(氧化铟锡)以的厚度被涂布成薄膜的玻璃基板放入溶解有洗涤剂的蒸馏水中,利用超声波进行洗涤。这时,洗涤剂使用菲希尔公司(Fischer Co.)制品,蒸馏水使用了利用密理博公司(Millipore Co.)制造的过滤器(Filter)过滤两次的蒸馏水。将ITO洗涤30分钟后,用蒸馏水重复两次而进行10分钟超声波洗涤。在蒸馏水洗涤结束后,用异丙醇、丙酮、甲醇的溶剂进行超声波洗涤并干燥后,输送至等离子体清洗机。此外,利用氧等离子体,将上述基板清洗5分钟后,将基板输送至真空蒸镀机。ITO (indium tin oxide) The glass substrate coated with a film of a thickness of 10000 mm was placed in distilled water dissolved with a detergent and washed with ultrasonic waves. At this time, the detergent used a product of Fischer Co., and the distilled water used distilled water filtered twice by a filter manufactured by Millipore Co. After ITO was washed for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After the distilled water washing was completed, ultrasonic washing was carried out with a solvent of isopropyl alcohol, acetone, and methanol and dried, and then transported to a plasma cleaning machine. In addition, after the above-mentioned substrate was cleaned for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.
在这样准备的ITO透明电极上,将由下述化学式HAT表示的化合物以的厚度进行热真空蒸镀而形成空穴注入层。在上述空穴注入层上,作为空穴传输层,将由下述化学式HT1表示的化合物以的厚度进行真空蒸镀后,作为电子阻挡层,将在上述合成例1中制造的化合物1以的厚度进行热真空蒸镀。接着,作为发光层,将由下述化学式BH表示的化合物和由下述化学式BD表示的化合物以25:1的重量比并以的厚度进行真空蒸镀。接着,作为空穴阻挡层,将由下述化学式HB1表示的化合物以的厚度进行真空蒸镀。接着,作为电子注入和传输层,将由下述化学式ET1表示的化合物和由下述LiQ表示的化合物以1:1的重量比并以的厚度进行热真空蒸镀。在上述电子传输和注入层上,依次将氟化锂(LiF)以的厚度、将铝以的厚度进行蒸镀而形成阴极,从而制造了有机发光器件。On the ITO transparent electrode prepared in this way, a compound represented by the following chemical formula HAT was applied as On the hole injection layer, a compound represented by the following chemical formula HT1 was deposited as a hole transport layer. After vacuum deposition with a thickness of , as an electron blocking layer, the compound 1 prepared in the above-mentioned Synthesis Example 1 was Next, as a light-emitting layer, a compound represented by the following chemical formula BH and a compound represented by the following chemical formula BD were prepared at a weight ratio of 25:1 and Next, as a hole blocking layer, a compound represented by the following chemical formula HB1 was deposited in the form of Next, as an electron injection and transport layer, a compound represented by the following chemical formula ET1 and a compound represented by the following LiQ were mixed at a weight ratio of 1:1 and On the electron transport and injection layers, lithium fluoride (LiF) is deposited in the form of The thickness of the aluminum A cathode is formed by evaporation with a thickness of , thereby manufacturing an organic light-emitting device.
实验例1-2至1-8和比较实验例1-1至1-3Experimental Examples 1-2 to 1-8 and Comparative Experimental Examples 1-1 to 1-3
在上述实验例1-1中,使用下述表1中记载的化合物代替化合物1,除此以外,通过与上述实验例1-1相同的方法制作了实验例1-2至1-8和比较实验例1-1至1-3的有机发光器件。对实验例和比较实验例中制造的有机发光器件施加10mA/cm2的电流时,测定了电压、效率、色坐标和寿命,将其结果示于下述表1。另一方面,T95表示亮度从初始亮度(6000尼特)减少至95%所需的时间。In the above-mentioned Experimental Example 1-1, the organic light-emitting devices of Experimental Examples 1-2 to 1-8 and Comparative Experimental Examples 1-1 to 1-3 were prepared by the same method as the above-mentioned Experimental Example 1-1, except that the compounds described in the following Table 1 were used instead of Compound 1. When a current of 10 mA/cm 2 was applied to the organic light-emitting devices manufactured in the Experimental Examples and Comparative Experimental Examples, the voltage, efficiency, color coordinates and life were measured, and the results are shown in the following Table 1. On the other hand, T95 represents the time required for the brightness to decrease from the initial brightness (6000 nits) to 95%.
[表1][Table 1]
如上述表1所示的那样,确认了本发明的化合物的电子阻挡能力优异,将其用于电子阻挡层的有机发光器件在驱动电压、效率和寿命方面显示出显著的效果。As shown in Table 1, it was confirmed that the compound of the present invention has excellent electron blocking ability, and an organic light-emitting device using the compound in an electron blocking layer exhibits remarkable effects in terms of driving voltage, efficiency and life.
将实验例1-1至1-8与比较实验例1-1至1-3进行比较,确认了本发明的化合物通过在四氢萘上具有碳原子数1至3的烷基取代基,并且在四氢萘的苯环部分具有烷基或芳基取代基,从而将其用于电子阻挡层的有机发光器件的驱动电压低、效率高、寿命长。By comparing Experimental Examples 1-1 to 1-8 with Comparative Experimental Examples 1-1 to 1-3, it was confirmed that the compounds of the present invention have an alkyl substituent having 1 to 3 carbon atoms on tetralin and an alkyl or aryl substituent on the benzene ring portion of tetralin, thereby enabling the organic light-emitting device using it as an electron blocking layer to have a low driving voltage, high efficiency and long life.
实验例2-1至2-14和比较实验例1-1、2-1至2-4Experimental Examples 2-1 to 2-14 and Comparative Experimental Examples 1-1, 2-1 to 2-4
在上述实验例1-1中,作为电子阻挡层,使用由上述化学式EB1表示的化合物代替化合物1,作为空穴传输层,使用下述表2中记载的化合物代替由上述化学式HT1表示的化合物,除此以外,通过与上述实验例1-1相同的方法制作了实验例2-1至2-14和比较实验例2-1至2-4的有机发光器件。对实验例和比较实验例中制造的有机发光器件施加10mA/cm2的电流时,测定了电压、效率、色坐标和寿命,将其结果示于下述表2。另一方面,T95表示亮度从初始亮度(6000尼特)减少至95%所需的时间In the above-mentioned Experimental Example 1-1, as an electron blocking layer, the compound represented by the above-mentioned chemical formula EB1 was used instead of compound 1, and as a hole transport layer, the compound described in the following Table 2 was used instead of the compound represented by the above-mentioned chemical formula HT1. In addition, the organic light-emitting devices of Experimental Examples 2-1 to 2-14 and Comparative Experimental Examples 2-1 to 2-4 were prepared by the same method as the above-mentioned Experimental Example 1-1. When a current of 10 mA/cm 2 was applied to the organic light-emitting devices manufactured in the Experimental Examples and Comparative Experimental Examples, the voltage, efficiency, color coordinates and life were measured, and the results are shown in the following Table 2. On the other hand, T95 represents the time required for the brightness to decrease from the initial brightness (6000 nits) to 95%.
[表2][Table 2]
如上述表2所示的那样,确认了本发明的化合物的空穴传输能力优异,将其用于空穴传输层的有机发光器件在驱动电压、效率和寿命方面显示出显著的效果。As shown in Table 2, it was confirmed that the compound of the present invention has excellent hole transporting ability, and an organic light-emitting device using the compound in a hole transporting layer exhibits remarkable effects in terms of driving voltage, efficiency and life.
将实验例2-1至2-14与比较实验例1-1、2-1和2-2进行比较,确认了本发明的化合物通过在四氢萘上具有碳原子数1至3的烷基取代基,并且在四氢萘的苯环部分具有烷基或芳基取代基,从而将其用于空穴传输层的有机发光器件的驱动电压低、效率高、寿命长。By comparing Experimental Examples 2-1 to 2-14 with Comparative Experimental Examples 1-1, 2-1 and 2-2, it was confirmed that the compounds of the present invention have an alkyl substituent having 1 to 3 carbon atoms on tetralin and an alkyl or aryl substituent on the benzene ring portion of tetralin, thereby enabling the organic light-emitting device using it as a hole transport layer to have a low driving voltage, high efficiency and long life.
将实验例2-1至2-14与比较实验例2-3和2-4进行比较,确认了在本发明的化合物中,特别是,在由化学式1表示的化合物中,R3和R4为芳基,或者与相邻的基团彼此结合而形成取代或未取代的烃环基的情况下,通过芴基的3号位置被芳基取代,将其用于空穴传输层的有机发光器件改善了空穴迁移特性,从而驱动电压低、效率高、寿命长。By comparing Experimental Examples 2-1 to 2-14 with Comparative Experimental Examples 2-3 and 2-4, it was confirmed that in the compounds of the present invention, in particular, in the compound represented by Chemical Formula 1, when R3 and R4 are aromatic groups, or are combined with adjacent groups to form a substituted or unsubstituted hydrocarbon ring group, the 3rd position of the fluorenyl group is replaced by an aromatic group, and the organic light-emitting device using it as a hole transport layer improves the hole migration characteristics, thereby having a low driving voltage, high efficiency and a long life.
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