Organic molecules for optoelectronic devices, compositions, optoelectronic devices, and methods for manufacturing optoelectronic devices
Purely organic molecules are developed to enhance the efficiency and stability of OLEDs by emitting in the blue, sky blue, or green spectral range, addressing the limitations of metal-complex emitters in optoelectronic devices.
Patent Information
- Application Number
- JP2022564154
- Authority / Receiving Office
- JP · JP
- Patent Type
- Patents
- Current Assignee / Owner
- Priority Date
- 2020-12-23
- Filing Date
- 2021-04-23
- Publication Date
- 2026-02-17
- Estimated Expiration
- 2041-04-23
AI Technical Summary
Existing optoelectronic devices, such as OLEDs, face challenges in achieving high efficiency and color purity, particularly in the blue, sky blue, or green spectral range, with existing metal-complex emitters exhibiting lower stability and efficiency.
Development of purely organic molecules without metal ions, specifically designed to emit in the desired spectral range with a photoluminescence quantum yield greater than 50%, enhancing device efficiency and stability.
The organic molecules provide increased efficiency and color purity in OLEDs with improved stability, as evidenced by a full width at half maximum (FWHM) of the emission, surpassing previous emitter materials.
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Figure 0007815141000001 
Figure 0007815141000002 
Figure 0007815141000003
Abstract
Description
[Technical Field]
[0001] The present invention relates to light-emitting organic molecules and their use in organic light-emitting diodes (OLEDs) and other optoelectronic devices. Summary of the Invention [Problem to be solved by the invention]
[0002] It is an object of the present invention to provide molecules suitable for use in optoelectronic devices. [Means for solving the problem]
[0003] Such objectives are achieved by the present invention, which provides a new class of organic molecules.
[0004] The organic molecules according to the invention are purely organic molecules and do not contain any metal ions, in contrast to the metal complexes known to be used in optoelectronic devices. [Effects of the Invention]
[0005] According to the present invention, the organic molecules exhibit an emission maximum in the blue, sky blue, or green spectral range. The organic molecules exhibit an emission maximum, in particular, between 420 nm and 520 nm, preferably between 440 nm and 495 nm, more preferably between 450 nm and 470 nm, or in particular, below 560 nm, more preferably below 550 nm, even more preferably below 545 nm or below 540 nm. The emission maximum of the organic molecules generally exhibits an emission maximum greater than 500 nm, more preferably greater than 510 nm, even more preferably above 515 nm or above 520 nm. The photoluminescence quantum yield of the organic molecules according to the present invention is particularly greater than 50%. The use of the molecules according to the present invention in optoelectronic devices, such as organic light-emitting diodes (OLEDs), leads to increased efficiency or color purity of the device, which is expressed by the full width at half maximum (FWHM) of the emission of the device. The corresponding OLEDs have higher stability than previously known emitter materials and OLEDs with similar hues. DETAILED DESCRIPTION OF THE INVENTION
[0006] The organic molecules of the present invention comprise or consist of the structure of Formula I:
[0007] [ka]
[0008] In Formula I, n is 0 or 1, X, in each occurrence, independently, is a direct bond, CR 3 R 4 , C=CR 3 R 4 , C=O, C=NR 3 , N.R. 3 , O, SiR 3 R 4 , S, S(O) and S(O)2; R 1 , R 2 , R3 , R 4 , R I , R II , R III , R IV and R V is, independently, Hydrogen, deuterium, N(R 5 )2, OR 5 , Si(R 5 )3, B(OR 5 )2, B(R 5 )2, OSO2R 5 , CF3, CN, F, Br, I, one or more substituents R 5 C1-C selectively substituted with 40 Alkyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C1-C selectively substituted with 40 Alkoxy, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C1-C selectively substituted with 40 thioalkoxy, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C2-C selectively substituted with 40 alkenyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C2-C selectively substituted with 40 Alkynyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C6-C selectively substituted with 60 aryl, and one or more substituents R 5 C2-C selectively substituted with 57 heteroaryl; R d and R e are independent of each other, Hydrogen, deuterium, CF3, CN, F, Br, I, one or more substituents R a C1-C selectively substituted with 40 Alkyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R a C6-C selectively substituted with 60 aryl, and one or more substituents R a C2-C selectively substituted with 57 heteroaryl; R a are in each case, independently of one another, Hydrogen, deuterium, N(R 5 )2, OR 5 , Si(R 5 )3, B(OR 5 )2, B(R 5 )2, OSO2R 5 , CF3, CN, F, Br, I, one or more substituents R 5 C1-C selectively substituted with 40 Alkyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5C1-C selectively substituted with 40 Alkoxy, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C1-C selectively substituted with 40 thioalkoxy, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C2-C selectively substituted with 40 alkenyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C2-C selectively substituted with 40 Alkynyl, where one or more non-adjacent CH groups are R 5 C=CR 5, C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C6-C selectively substituted with 60 aryl, and one or more substituents R 5 C2-C selectively substituted with 57 heteroaryl; R 5 are in each case, independently of one another, Hydrogen, deuterium, N(R 6 )2, OR 6 , Si(R 6 )3, B(OR 6 )2, B(R 6 )2, OSO2R 6 , CF3, CN, F, Br, I, one or more substituents R 6 C1-C selectively substituted with 40 Alkyl, where one or more non-adjacent CH groups are R 6 C=CR 6 , C≡C, Si(R 6 )2, Ge(R 6 )2, Sn(R 6 )2, C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO2, NR 6 , O, S or CONR 6 is selectively substituted with one or more substituents R 6 C1-C selectively substituted with 40 Alkoxy, where one or more non-adjacent CH groups are R 6 C=CR 6 , C≡C, Si(R 6 )2, Ge(R 6 )2, Sn(R6 )2, C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO2, NR 6 , O, S or CONR 6 is selectively substituted with one or more substituents R 6 C1-C selectively substituted with 40 thioalkoxy, where one or more non-adjacent CH groups are R 6 C=CR 6 , C≡C, Si(R 6 )2, Ge(R 6 )2, Sn(R 6 )2, C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO2, NR 6 , O, S or CONR 6 is selectively substituted with one or more substituents R 6 C2-C selectively substituted with 40 alkenyl, where one or more non-adjacent CH groups are R 6 C=CR 6 , C≡C, Si(R 6 )2, Ge(R 6 )2, Sn(R 6 )2, C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO2, NR 6 , O, S or CONR 6 is selectively substituted with one or more substituents R 6 C2-C selectively substituted with 40 Alkynyl, where one or more non-adjacent CH groups are R 6 C=CR 6 , C≡C, Si(R 6 )2, Ge(R 6 )2, Sn(R 6 )2, C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO2, NR 6, O, S or CONR 6 is selectively substituted with one or more substituents R 6 C6-C selectively substituted with 60 aryl, and one or more substituents R 6 C2-C selectively substituted with 57 heteroaryl; R 6 are in each case, independently of one another, Hydrogen, deuterium, OPh, CF3, CN, F, C1-C5 alkyl, wherein one or more hydrogen atoms are optionally replaced, independently of one another, by deuterium, CN, CF or F; C1-C5 alkoxy, wherein one or more hydrogen atoms are optionally replaced, independently of one another, by deuterium, CN, CF or F; C1-C5 thioalkoxy, wherein one or more hydrogen atoms are optionally replaced, independently of one another, by deuterium, CN, CF or F; C2-C5 alkenyl, wherein one or more hydrogen atoms are optionally replaced, independently of one another, by deuterium, CN, CF or F; C2-C5 alkynyl, wherein one or more hydrogen atoms are optionally replaced, independently of one another, by deuterium, CN, CF or F; C6-C optionally substituted with one or more C1-C5 alkyl substituents 18 aryl, C2-C optionally substituted with one or more C1-C5 alkyl substituents 17 heteroaryl, N(C6-C 18 aryl)2, N(C2-C 17 heteroaryl)2, and N(C2-C 17 Heteroaryl)(C6-C 18 aryl), The substituent R a ,Rd ,R e ,R 5 are, independently of one another, one or more substituents R a ,R d ,R e ,R 5 with which selectively form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system; The substituent R 1 ,R 2 ,R 3 ,R 4 ,R 5 ,R I ,R II ,R III ,R IV ,R V are, independently of one another, one or more substituents R 1 ,R 2 ,R 3 ,R 4 ,R 5 ,R I ,R II ,R III ,R IV ,R V with the optionally forming a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0009] Substituent R a ,R d ,R e ,R 1 ,R 2 ,R 3 ,R 4 ,R 5 ,R I ,R II ,R III ,R IV ,R V Examples of C6-C 60 Aryl, preferably C-C 30 Aryl, more preferably C-C 18 aryl, and even more preferably C-C 10 It may also include aryl.
[0010] Exemplary aryl substituents include monocyclic benzene, bicyclic biphenyl, fused bicyclic naphthalene, tricyclic terphenyl (m-terphenyl, o-terphenyl, p-terphenyl), fused tricyclic ring systems such as acenaphthylene-fluorene-phenalene-phenanthrene, fused tetracyclic ring systems such as triphenylene-pyrene-naphthacene, and fused pentacyclic ring systems such as perylene-pentacene.
[0011] Substituent R a ,R d ,R e ,R 1 ,R 2 ,R 3 ,R 4 ,R 5 ,R I ,R II ,R III ,R IV ,R V An example of this is C2-C 57 Heteroaryl, preferably C-C 30 Heteroaryl, more preferably C-C 17 Heteroaryl, even more preferably C-C 10 It also includes heteroaryl.
[0012] Illustrative heteroaryl substituents also include pyrrole, oxazole, isoxazole, thiazole, isothiazole, imidazole, oxadiazole, thiadiazole, triazole, tetrazole, pyrazole, pyridine, pyrimidine, pyridazine, pyrazine, triazine, indole, isoindole, 1H-indazole, benzimidazole, benzoxazole, benzothiazole, 1H-benzotriazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, phthalazine, naphthyridine, purine, pteridine, carbazole, acridine, phenoxathiin, phenoxazine ring, phenothiazine, phenazine, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, dibenzothiophene, furazan, oxadiazole, and thianthrene.
[0013] Substituent Ra ,R d ,R e ,R 1 ,R 2 ,R 3 ,R 4 ,R 5 ,R I ,R II ,R III ,R IV ,R V Examples of C1-C 40 Alkyl, preferably C1-C 24 Alkyl, or branched or cyclic C3-C 40 Alkyl, more preferably C-C 18 Alkyl, or branched or cyclic C3-C 18 Alkyl, more preferably C-C 12 Alkyl, or branched or cyclic C3-C 12 It also includes alkyl, even more preferably C1-C6 alkyl, or branched or cyclic C3-C6 alkyl, particularly preferably C1-C4 alkyl or branched C3-C4 alkyl.
[0014] Specific alkyl substituents are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methyl, pentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl. and n-octadecyl such as n-octadecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-oct ...
[0015] Substituent R a ,R d ,R e ,R1 ,R 2 ,R 3 ,R 4 ,R 5 ,R I ,R II ,R III ,R IV ,R V Examples of C1-C 40 Alkoxy, preferably C-C 24 Alkoxy or branched or cyclic C3-C 40 Alkoxy, more preferably C-C 18 Alkoxy or branched or cyclic C3-C 18 Alkoxy, more preferably C-C 12 Alkoxy or branched or cyclic C3-C 12 It also includes alkoxy, even more preferably C1-C6 alkoxy, or branched or cyclic C3-C6 alkoxy, particularly preferably C1-C4 alkoxy or branched C3-C4 alkoxy.
[0016] Specific alkoxy substituents also include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, and the like.
[0017] Substituent R a ,R d ,R e ,R 1 ,R 2 ,R 3 ,R 4 ,R 5 ,R I ,R II ,R III ,R IV ,R V Examples of C1-C 40 Thioalkyl, preferably C-C 24 Thioalkyl, or branched or cyclic C3-C 40 Thioalkyl, more preferably C-C 18 Thioalkyl, or branched or cyclic C3-C18 Thioalkyl, more preferably C-C 12 Thioalkyl, or branched or cyclic C3-C 12 It also includes thioalkyl, even more preferably C1-C6 thioalkyl, or branched or cyclic C3-C6 thioalkyl, particularly preferably C1-C4 thioalkyl or branched C3-C4 thioalkyl.
[0018] Substituent R a ,R d ,R e ,R 1 ,R 2 ,R 3 ,R 4 ,R 5 ,R I ,R II ,R III ,R IV ,R V An example of this is C2-C 40 Alkenyl, preferably C-C 24 Alkenyl, or branched or cyclic C3-C 40 Alkenyl, more preferably C-C 18 Alkenyl, or branched or cyclic C3-C 18 Alkenyl, more preferably C-C 12 Alkenyl, or branched or cyclic C3-C 12 It also includes alkenyl, even more preferably C2-C6 alkenyl, or branched or cyclic C3-C6 alkenyl, particularly preferably C1-C4 alkenyl or branched C3-C4 alkenyl.
[0019] Substituent R a ,R d ,R e ,R 1 ,R 2 ,R 3 ,R 4 ,R 5 ,R I ,R II ,R III ,R IV ,R V Examples of C1-C 40Alkynyl, preferably C-C 24 Alkynyl, or branched or cyclic C3-C 40 Alkynyl, more preferably C-C 18 Alkynyl, or branched or cyclic C3-C 18 Alkynyl, more preferably C-C 12 Alkynyl, or branched or cyclic C3-C 12 It also includes alkynyl, even more preferably C2-C6 alkynyl, or branched or cyclic C3-C6 alkynyl, particularly preferably C1-C4 alkynyl or branched C3-C4 alkynyl.
[0020] In one embodiment, R 1 , R 2 , R 3 , R 4 , R I , R II , R III , R IV , R V are independent of each other, hydrogen, deuterium, N(R 5 )2, OR 5 , SR 5 , Si(R 5 )3. B(OR 5 )2, B(R 5 )2, OSO2R 5 , CF3, CN, halogen, one or more substituents R 5 C1-C selectively substituted with 18 Alkyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5)2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C1-C selectively substituted with 18 Alkoxy, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C1-C selectively substituted with 18 thioalkoxy, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C2-C selectively substituted with 18 alkenyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR5 is selectively substituted with one or more substituents R 5 C2-C selectively substituted with 18 Alkynyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C6-C selectively substituted with 18 aryl, and one or more substituents R 5 C2-C selectively substituted with 17 Heteroaryl is selected from the group consisting of: R 5 are in each case, independently of one another, Hydrogen, deuterium, N(R 6 )2, OR 6 , Si(R 6 )3, B(OR 6 )2, B(R 6 )2, OSO2R 6 , CF3, CN, F, Br, I, one or more substituents R 6 C1-C selectively substituted with 18 Alkyl, where one or more non-adjacent CH groups are R 6 C=CR 6 , C≡C, Si(R 6 )2, Ge(R 6 )2, Sn(R 6 )2, C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO2, NR 6 , O, S or CONR 6 is selectively substituted with one or more substituents R 6C1-C selectively substituted with 18 Alkoxy, where one or more non-adjacent CH groups are R 6 C=CR 6 , C≡C, Si(R 6 )2, Ge(R 6 )2, Sn(R 6 )2, C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO2, NR 6 , O, S or CONR 6 is selectively substituted with one or more substituents R 6 C1-C selectively substituted with 18 thioalkoxy, where one or more non-adjacent CH groups are R 6 C=CR 6 , C≡C, Si(R 6 )2, Ge(R 6 )2, Sn(R 6 )2, C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO2, NR 6 , O, S or CONR 6 is selectively substituted with one or more substituents R 6 C2-C selectively substituted with 18 alkenyl, where one or more non-adjacent CH groups are R 6 C=CR 6 , C≡C, Si(R 6 )2, Ge(R 6 )2, Sn(R 6 )2, C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO2, NR 6 , O, S or CONR 6 is selectively substituted with one or more substituents R 6 C2-C selectively substituted with 18 Alkynyl, Here, one or more non-adjacent CH 2 The group is R 6 C=CR6 , C≡C, Si(R 6 )2, Ge(R 6 )2, Sn(R 6 )2, C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO2, NR 6 , O, S or CONR 6 is selectively substituted with one or more substituents R 6 C6-C selectively substituted with 18 aryl, and one or more substituents R 6 C2-C selectively substituted with 17 It is also selected from the group consisting of heteroaryl.
[0021] In one preferred embodiment, n is also 1. In another embodiment, n is also 0. In one preferred embodiment, R 1 , R 2 , R 3 , R 4 , R I , R II , R III , R IV , R V are independent of each other, hydrogen, deuterium, N(R 5 )2, OR 5 , Si(R 5 )3. B(R 5 )2, CF3, CN, halogen, one or more substituents R 5 C1-C selectively substituted with 18 Alkyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C6-C selectively substituted with 18 aryl, and one or more substituents R 5 C2-C selectively substituted with 17 heteroaryl; R 5 are in each case, independently of one another, hydrogen, deuterium, N(R 6 )2, OR 6 , Si(R 6 )3, B(R 6 )2, CF 3 ,CN,F,Br,I, one or more substituents R 6 C1-C selectively substituted with 18 Alkyl, where one or more non-adjacent CH groups are R 6 C=CR 6 , C≡C, Si(R 6 )2, Ge(R 6 )2, Sn(R 6 )2, C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO2, NR 6 , O, S or CONR 6 is selectively substituted with one or more substituents R 6 C6-C selectively substituted with 18 aryl, and one or more substituents R 6 C2-C selectively substituted with 17 It is also selected from the group consisting of heteroaryl.
[0022] In one preferred embodiment, R 1 , R 2 , R 3 , R 4 , RI , R II , R III , R IV , R V are independent of each other, hydrogen, deuterium, N(R 5 )2, OR 5 , Si(R 5 )3. B(R 5 )2, CF3, CN, halogen, one or more substituents R 5 C1-C selectively substituted with 18 Alkyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C6-C selectively substituted with 18 aryl, and one or more substituents R 5 C2-C selectively substituted with 17 heteroaryl; R 5 are in each case, independently of one another, Hydrogen, deuterium, N(R 6 )2, OR 6 , Si(R 6 )3, B(R 6 )2, CF3, CN, F, Br, I, one or more substituents R 6 C1-C selectively substituted with 18 Alkyl, where one or more non-adjacent CH groups are R6 C=CR 6 , C≡C, Si(R 6 )2, Ge(R 6 )2, Sn(R 6 )2, C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO2, NR 6 , O, S or CONR 6 is selectively substituted with one or more substituents R 6 C6-C selectively substituted with 18 aryl, and one or more substituents R 6 C2-C selectively substituted with 17 heteroaryl; R 1 , R 2 , R 3 , R I , R II , R III , R IV , R 5 , R V can be optionally joined together to form an aryl or heteroaryl ring optionally substituted with one or more C1-C5 alkyl substituents, deuterium, halogen, CN, or CF3.
[0023] In one preferred embodiment, R 1 , R 2 , R 3 , R 4 , R I , R II , R III , R IV , R V are independent of each other, hydrogen, deuterium, N(R 5 )2, OR 5 , Si(R 5 ) 3 , B(R 5 )2, CF3, CN, halogen, one or more substituents R 5 C1-C selectively substituted with 18 Alkyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C6-C selectively substituted with 18 aryl, and one or more substituents R 5 C2-C selectively substituted with 17 heteroaryl; R 5 are in each case, independently of one another, Hydrogen, deuterium, N(R 6 )2, OR 6 , Si(R 6 )3, B(R 6 )2, CF3, CN, F, Br, I, C1-C optionally substituted with one or more substituents R6 18 Alkyl, where one or more non-adjacent CH groups are R 6 C=CR 6 , C≡C, Si(R 6 )2, Ge(R 6 )2, Sn(R 6 )2, C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO2, NR 6 , O, S or CONR 6 is selectively substituted with one or more substituents R 6 C6-C selectively substituted with 18 aryl, and C2-C optionally substituted with one or more substituents R6 17 heteroaryl; R located adjacent to each other 1 , R 2 , R I , R II , R III , R IV , R 5 , R V can be optionally joined together to form an aryl or heteroaryl ring optionally substituted with one or more C1-C5 alkyl substituents, deuterium, halogen, CN, or CF3.
[0024] In one preferred embodiment, R 1 , R 2 , R 3 , R 4 , R I , R II , R III , R IV , R V are independent of each other, hydrogen, deuterium, N(R 5 )2, OR 5 , Si(R 5 )3. B(R 5 )2, CF3, CN, halogen, one or more substituents R 5 C1-C selectively substituted with 18 Alkyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C6-C selectively substituted with 18 aryl, and one or more substituents R 5 C2-C selectively substituted with 17 heteroaryl; R 5 are in each case, independently of one another, Hydrogen, deuterium, N(R 6 )2, OR 6 , Si(R 6 )3, B(R 6 )2, CF3, CN, F, Br, I, one or more substituents R 6 C1-C selectively substituted with 18 Alkyl, where one or more non-adjacent CH groups are R 6 C=CR 6 , C≡C, Si(R 6 )2, Ge(R 6 )2, Sn(R 6 )2, C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO2, NR 6 , O, S or CONR 6 is selectively substituted with one or more substituents R 6 C6-C selectively substituted with 18 aryl, and one or more substituents R 6 C2-C selectively substituted with 17 It is also selected from the group consisting of heteroaryl.
[0025] In one embodiment, R 1 , R 2 , R 3 , R 4 , R I , R II , R III , R IV , R V are independent of each other, hydrogen, deuterium, one or more substituents R 5 C1-C selectively substituted with 18 Alkyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C6-C selectively substituted with 18 aryl, and one or more substituents R 5 C2-C selectively substituted with 17 It is also selected from the group consisting of heteroaryl.
[0026] In one embodiment, R 1 , R 2 , R I , R II , R III , R IV , R V are independent of each other, hydrogen, deuterium, one or more substituents R 5 C1-C selectively substituted with 18 Alkyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C6-C selectively substituted with 18aryl, and one or more substituents R 5 C2-C selectively substituted with 17 heteroaryl; R located adjacent to each other 1 , R 2 , R I , R II , R III , R IV , R V can be optionally joined together to form an aryl or heteroaryl ring optionally substituted with one or more C1-C5 alkyl substituents, deuterium, halogen, CN, or CF3.
[0027] In one embodiment, R 3 , R 4 are independent of each other, one or more substituents R 5 C1-C selectively substituted with 18 Alkyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C6-C selectively substituted with 18 aryl, and one or more substituents R 5 C2-C selectively substituted with 17 It is also selected from the group consisting of heteroaryl.
[0028] In one embodiment, R 1 , R 2 , R 3 , R 4 , R I , R II , R III, R IV , R V are independent of each other, one or more substituents R 5 C1-C selectively substituted with 18 Alkyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C6-C selectively substituted with 18 aryl, and one or more substituents R 5 C2-C selectively substituted with 17 It is also selected from the group consisting of heteroaryl.
[0029] In other embodiments, R 1 , R 2 , R 3 , R 4 , R I , R II , R III , R IV , R V are independent of each other, one or more substituents R 5 C6-C selectively substituted with 18 aryl, and one or more substituents R 5 C2-C selectively substituted with 17 It is also selected from the group consisting of heteroaryl.
[0030] In yet another embodiment, R 1 , R 2 , R 3 , R 4 , R I , R II , R III, R IV , R V are independent of each other, one or more substituents R 5 C6-C selectively substituted with 18 It is also selected from the group consisting of aryl.
[0031] In one preferred embodiment, R 3 are independent of each other, one or more substituents R 5 C1-C selectively substituted with 40 Alkyl, one or more substituents R 5 C6-C selectively substituted with 18 aryl, and one or more substituents R 5 C2-C selectively substituted with 17 It is also selected from the group consisting of heteroaryl.
[0032] In one preferred embodiment, R 3 are independent of each other, one or more substituents R 5 C6-C selectively substituted with 18 aryl, and one or more substituents R 5 C2-C selectively substituted with 17 It is also selected from the group consisting of heteroaryl.
[0033] In a further preferred embodiment, R 3 are independent of each other, one or more substituents R 5 C6-C selectively substituted with 18 It is also selected from the group consisting of aryl.
[0034] In a further preferred embodiment, R 3 is one or more substituents R 6 C6-C selectively substituted with 18 It is aryl.
[0035] In a further preferred embodiment, R3 is one or more substituents R 5 and optionally substituted phenyl (Ph).
[0036] In one embodiment, R 3 is one or more substituents R 6 is phenyl optionally substituted with
[0037] In one embodiment, R 3 is phenyl optionally substituted with one or more C1-C5 alkyl substituents.
[0038] In one embodiment, R 3 are independent of each other, one or more C1-C5 alkyl groups; wherein one or more hydrogen atoms are optionally replaced, independently of one another, by deuterium, CN, CF or F; C6-C optionally substituted with one or more C1-C5 alkyl substituents 18 aryl, and C2-C optionally substituted with one or more C1-C5 alkyl substituents 17 It is phenyl optionally substituted with heteroaryl.
[0039] In one embodiment, R 3 is Ph.
[0040] In one embodiment, R 1 , R 2 , R 3 , R 4 , R I , R II , R III , R IV , R V are independent of each other, one or more substituents R 5 C1-C selectively substituted with 18 alkyl; where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 may be selectively substituted with In one embodiment, R 1 , R 2 , R I , R II , R III , R IV , R V and R a At least one substituent selected from the group consisting of one or more substituents R 5 C1-C selectively substituted with 18 is alkyl, Here, one or more non-adjacent CH 2 The group is R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 may be selectively substituted with
[0041] In one embodiment, R 1 , R 2 , R I , R II , R III , R IV , R V and R a At least one substituent selected from the group consisting of: Me, i Pr, t It's Bu. In one embodiment, R a are in each case, independently of one another, hydrogen, deuterium, one or more substituents R 5 C1-C selectively substituted with 18 Alkyl, one or more substituents R 5 C6-C selectively substituted with 18 aryl, and one or more substituents R 5 C2-C selectively substituted with 17 It is also selected from the group consisting of heteroaryl.
[0042] In one embodiment, R a are in each case, independently of one another, hydrogen, deuterium, one or more substituents R 5 C1-C selectively substituted with 18 Alkyl, and one or more substituents R 5 C6-C selectively substituted with 18 It is also selected from the group consisting of aryl.
[0043] In one embodiment, R a are in each case, independently of one another, hydrogen, deuterium, one or more substituents R 5 C1-C selectively substituted with 18 It is also selected from the group consisting of alkyl.
[0044] In one embodiment, at least one R a teeth, Me, i Pr, t It's Bu.
[0045] In one preferred embodiment, R 1 , R 2 , R I , R II , R III , R IV , R VAt least one substituent selected from the group consisting of one or more substituents R 1 ,R 2 ,R 3 ,R 4 ,R 5 ,R I ,R II ,R III ,R IV ,R V together can form mono- or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring systems.
[0046] In a further preferred embodiment, R 1 , R 2 , R I , R II , R III , R IV , R V At least one substituent selected from the group consisting of one or more substituents R 1 ,R 2 ,R 3 ,R 4 ,R 5 ,R I ,R II ,R III ,R IV ,R V together can form aromatic benzo-fused ring systems and / or heteroaromatic benzo-fused ring systems.
[0047] In some embodiments, R 1 , R 2 , R I , R II , R III , R IV , R V At least one substituent selected from the group consisting of one or more adjacent substituents R 1 ,R 2 ,R I ,R II ,R III ,R IV and R V together form an aromatic benzo-fused ring system and / or a heteroaromatic benzo-fused ring system,
[0048] Preferably, R 1 is R I Located adjacent to R I is R II and R 1 Located adjacent to R II is R III and R I Located adjacent to R III is R II Located adjacent to R 2 is R V Located adjacent to R V is R 2 and R IV Located adjacent to R IV is R V It may be located adjacent to
[0049] In some embodiments, R 1 , R 2 , R I , R II , R III , R IV , R V At least one substituent selected from the group consisting of one or more adjacent substituents R 1 ,R 2 ,R I ,R II ,R III ,R IV and R V together can form mono- or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring systems.
[0050] Preferably, R 1 is R I Located adjacent to R I is R II and R 1 Located adjacent to R II is R III and R I Located adjacent to R III is R II Located adjacent to R 2 is R VLocated adjacent to R V is R 2 and R IV Located adjacent to R IV is R V It may be located adjacent to
[0051] In one preferred embodiment, R 1 , R 2 , R I , R II , R III , R IV , R V At least one substituent selected from the group consisting of one or more substituents R 1 ,R 2 ,R 3 ,R 4 ,R 5 ,R I ,R II ,R III ,R IV , R V together to form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system, said ring system being selected from the group consisting of:
[0052] [ka]
[0053] Here, each dotted line represents a binding site.
[0054] In one preferred embodiment, R 1 , R 2 , R I , R II , R III , R IV , and R V At least one substituent selected from the group consisting of one or more substituents R 1 ,R 2 ,R 3 ,R 4 ,R 5 ,R I ,R II ,R III ,RIV , R V together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system, said ring system being selected from the group consisting of:
[0055] [ka]
[0056] Here, each dotted line represents a binding site.
[0057] In a preferred embodiment, the binding sites are located adjacent to each other, i.e., R 1 Preferably, R I Together with R, they form a ring system. I is preferably R II and / or R 1 forms a ring system with R II is preferably R III and / or R I forms a ring system with R III is preferably R II forms a ring system with R 2 is preferably R V and preferably R 2 and / or R IV forms a ring system with R IV is preferably R V This means that it forms a ring system with
[0058] Specific examples are as follows:
[0059] [ka]
[0060] In one embodiment, R 1 , R 2 , R I , R II , R III , R IV , R VAt least one substituent selected from the group consisting of one or more substituents R 1 ,R 2 ,R I ,R II ,R III ,R IV , R V together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system, said ring system being selected from the group consisting of:
[0061] [ka]
[0062] where X 1 is S, O or NR 5 is.
[0063] In a preferred embodiment of the organic molecule, the binding sites are positioned adjacent to each other (with no atoms between them).
[0064] In another embodiment, R 1 , R I , R II and R III At least one substituent selected from the group consisting of one or more substituents R 1 ,R I ,R II and R III together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system, said ring system being selected from the group consisting of:
[0065] [ka]
[0066] Here, each dotted line represents a binding site.
[0067] In yet another embodiment, R 1 , R I , RII and R III At least one substituent selected from the group consisting of one or more substituents R 1 ,R I ,R II and R III together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system, said ring system being selected from the group consisting of:
[0068] [ka]
[0069] Here, each dotted line represents a binding site.
[0070] In a preferred embodiment, the binding sites are located adjacent to each other, i.e., R 1 Preferably, R I forms a ring system with R I is preferably R II and / or R 1 forms a ring system with R II is preferably R III and / or R I Together with R, they form a ring system. III is preferably R II It means that the ring system is formed together with
[0071] In one embodiment, R 1 , R 2 , R I , R II , R III , R IV , R V At least one substituent selected from the group consisting of one or more substituents R 1 ,R 2 ,R I ,R II ,R III ,R IV , R Vtogether form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system, said ring system being selected from the group consisting of:
[0072] [ka]
[0073] where X 2 is N or CR 5 and X 3 is N or CR 5 is.
[0074] In a preferred embodiment, the binding sites are located adjacent to each other.
[0075] In one preferred embodiment, R d and R e are in each case, independently of one another, Hydrogen, deuterium, CF3, CN, F, Br, I, one or more substituents R a C1-C selectively substituted with 18 Alkyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R a C6-C selectively substituted with 18 aryl, and one or more substituents R a C2-C selectively substituted with 17 It is also selected from the group consisting of heteroaryl.
[0076] In one preferred embodiment, R a are in each case, independently of one another, hydrogen, deuterium, N(R 5 )2, OR 5 , SR 5 , Si(R 5 )3. B(OR 5 )2, B(R 5 )2, OSO2R 5 , CF3, CN, halogen, one or more substituents R 5 C1-C selectively substituted with 18 Alkyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C1-C selectively substituted with 18 Alkoxy, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5C1-C selectively substituted with 18 thioalkoxy, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C2-C selectively substituted with 18 alkenyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C2-C selectively substituted with 18 Alkynyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C6-C selectively substituted with 18 aryl, and one or more substituents R 5 C2-C selectively substituted with17 It is also selected from the group consisting of heteroaryl.
[0077] In one embodiment, at least one R a is different from hydrogen.
[0078] In one embodiment, R a are in each case, independently of one another, hydrogen, deuterium, N(R 5 )2, one or more substituents R 5 C1-C selectively substituted with 18 Alkyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C6-C selectively substituted with 18 aryl, and one or more substituents R 5 C2-C selectively substituted with 17 heteroaryl; or one or more substituents R a and R 5 together can form mono- or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring systems.
[0079] In one embodiment, R a are in each case, independently of one another, hydrogen, deuterium, N(R 5 )2, one or more substituents R5 C1-C selectively substituted with 18 Alkyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C6-C selectively substituted with 18 aryl, and one or more substituents R 5 C2-C selectively substituted with 17 heteroaryl; or one or more substituents R a and R 5 together can form an aromatic or heteroaromatic ring system.
[0080] In one embodiment of the present invention, R a are in each case, independently of one another, hydrogen, Me, i Pr, t Bu, CN, CF3, F, Me, i Pr, t aryl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F and Ph; Me, i Pr, t pyridinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F and Ph; Me, i Pr, t carbazolyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF, F and Ph; Me,i Pr, t triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F and Ph; Me, i Pr, t N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu, F, and Ph; R located adjacent to each other a The groups are optionally linked to each other and include one or more C1-C5 alkyl substituents, C6-C 18 The aryl or heteroaryl rings can be formed optionally substituted with aryl substituents, deuterium, halogen, CN, or CF3.
[0081] In one embodiment of the present invention, R a are in each case, independently of one another, hydrogen, Me, i Pr, t Bu, CN, CF3, F, Me, i Pr, t aryl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F and Ph; Me, i Pr, t pyridinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F and Ph; Me, i Pr, t carbazolyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF, F and Ph; Me, i Pr, t triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F and Ph; Me, i Pr, tIt is also selected from the group consisting of N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu, F, and Ph.
[0082] In yet another embodiment of the present invention, R a are in each case, independently of one another, hydrogen, Me, i Pr, t Bu, F, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F and Ph; Me, i Pr, t Carbazolyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F, and Ph; Me, i Pr, t It is also selected from the group consisting of N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu, F, and Ph.
[0083] In one embodiment of the present invention, R a are in each case, independently of one another, hydrogen, Me, i Pr, t Bu, F, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F and Ph; Me, i Pr, t Carbazolyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F, and Ph; Me, i Pr, tN(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu, F, and Ph; R located adjacent to each other a The groups are optionally linked to each other and include one or more C1-C5 alkyl substituents, C6-C 18 The aryl or heteroaryl rings can be formed optionally substituted with aryl substituents, deuterium, halogen, CN, or CF3.
[0084] In yet another embodiment of the present invention, R a are in each case, independently of one another, hydrogen, Me, i Pr, t Bu, F, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, F, and Ph; Me, i Pr, t carbazolyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, F, and Ph; Me, i Pr, t It is also selected from the group consisting of N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu, F, and Ph.
[0085] In yet another embodiment of the present invention, R a are in each case, independently of one another, hydrogen, Me, i Pr, t Bu, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph; Me, i Pr, tcarbazolyl optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph; Me, i Pr, t It is also selected from the group consisting of N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.
[0086] In yet another embodiment of the present invention, R a are in each case, independently of one another, hydrogen, Me, i Pr, t Bu, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph; and Me, i Pr, t It is also selected from the group consisting of N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.
[0087] In yet another embodiment of the present invention, R a are in each case, independently of one another, hydrogen, Me, i Pr, t Bu, and Me, i Pr, t It is also selected from the group consisting of Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.
[0088] In one embodiment, R a are in each case, independently of one another, hydrogen, deuterium, N(R 5 )2, one or more substituents R 5 C1-C selectively substituted with 18 Alkyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C6-C selectively substituted with 18 aryl, and one or more substituents R 5 C2-C selectively substituted with 17 heteroaryl; or one or more substituents R a and R 5 together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system, said ring system being selected from the group consisting of:
[0089] [ka]
[0090] Here, each dotted line represents a binding site.
[0091] In one embodiment, R a are in each case, independently of one another, hydrogen, deuterium, N(R 5 )2, one or more substituents R 5 C1-C selectively substituted with 18 Alkyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5)2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C6-C selectively substituted with 18 aryl, and one or more substituents R 5 C2-C selectively substituted with 17 heteroaryl; or one or more substituents R a and R 5 together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system, said ring system being selected from the group consisting of:
[0092] [ka]
[0093] Here, each dotted line represents a binding site.
[0094] In a preferred embodiment, the binding sites are located adjacent to each other, i.e., R a Preferably, R are located adjacent to each other. a It means that the ring system is formed together with
[0095] Specific examples are as follows:
[0096] [ka]
[0097] [ka]
[0098] [ka]
[0099] In one embodiment, at least one R a is one or more substituents Ra and R 5 together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system, said ring system being selected from the group consisting of:
[0100] [ka]
[0101] where X 1 is S, O or NR 5 is.
[0102] In a preferred embodiment, the binding sites are located adjacent to each other.
[0103] In a preferred embodiment, an organic molecule of the present invention comprises or consists of a structure of Formula I, where X is NR 3 and R d and R e are linked together to form an aromatic ring system, and R V is N(R 5 )2 or one or more substituents R 2 ,R 3 ,R 5 and R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0104] Specific examples are as follows: [ka]
[0105] In a preferred embodiment, an organic molecule of the present invention comprises or consists of a structure of Formula I, where X is NR 3 and R d and R e are linked together to form an aromatic ring system, and R V is N(R 6 )2 or one or more substituents R 2 ,R 3 ,R 5 and R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0106] In a preferred embodiment, an organic molecule of the present invention comprises or consists of a structure of Formula I, where X is NR 3 and R d and R e are linked together to form an aromatic ring system, and R V is N(R 5 )2 or one or more adjacent substituents R 2 and adjacent substituent R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0107] In a preferred embodiment, an organic molecule of the present invention comprises or consists of a structure of Formula I, where X is NR 3 and R d and R e are linked together to form an aromatic ring system, and R V is N(R 6 )2 or one or more adjacent substituents R 2 and adjacent substituent R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0108] In a preferred embodiment, an organic molecule of the present invention comprises or consists of a structure of Formula I, where X is NR 3 and R d and R e are linked together to form an aromatic ring system, and R V is N(R 5 )2. In a preferred embodiment, an organic molecule of the present invention comprises or consists of a structure of Formula I, where X is NR 3 and R d and R e are linked together to form an aromatic ring system, and R V is N(R 6 )2.
[0109] In a preferred embodiment, an organic molecule of the present invention comprises or consists of a structure of Formula I, where X is NR 3 and R d and R e are linked together to form an aromatic ring system, and R V is one or more substituents R 2 ,R 3 ,R 5 and R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0110] In a preferred embodiment, an organic molecule of the present invention comprises or consists of a structure of Formula I, where X is NR 3 and R d and R e are linked together to form an aromatic ring system, and R V is one or more adjacent substituents R 2 and / or adjacent substituent R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0111] Examples involving different substituents X and n=0 and n=1 are as follows:
[0112] [ka]
[0113] [ka]
[0114] Further examples of organic molecules according to the present invention also include:
[0115] [ka]
[0116] In a preferred embodiment, X is, in each occurrence independently of one another, a direct bond, NR 3 , C.R. 3 It is also selected from the group consisting of R4, S and O.
[0117] In a further preferred embodiment, X is, at each occurrence independently of one another, a direct bond, NR 3 , S and O.
[0118] In one embodiment, X, at each occurrence, independently, is a direct bond and NR 3 It is also selected from the group consisting of:
[0119] In one embodiment of the present invention, R 1 , R 2 , R 3 , R 4 , R I , R II , R III , R IV and R V are in each case, independently of one another, hydrogen, Me, i Pr, t Bu, CN, CF3, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t pyridinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3 and Ph; Me, i Pr, t pyrimidinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3 and Ph; Me, i Pr, t carbazolyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3 and Ph; Me, i Pr, t triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; It is also selected from the group consisting of N(Ph)2.
[0120] In one embodiment of the present invention, the organic molecule comprises or consists of the structure of Formula II:
[0121] [ka]
[0122] In one preferred embodiment of the invention, X is also, in each occurrence independently of one another, selected from the group consisting of a direct bond, NR3 and O.
[0123] In a preferred embodiment, an organic molecule of the present invention comprises or consists of a structure of Formula II, where X is NR 3 and R d and R e are linked together to form an aromatic ring system, and R V is N(R 5 )2 or one or more substituents R 2 ,R 3 ,R 5 and R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0124] In a preferred embodiment, an organic molecule of the present invention comprises or consists of a structure of Formula II, where X is NR 3 and R d and R e are linked together to form an aromatic ring system, and R V is N(R 5 )2 or one or more adjacent substituents R 2 and / or adjacent substituent R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0125] In one embodiment of the present invention, the organic molecule comprises or consists of the structure of Formula II-1:
[0126] [ka]
[0127] where R 3 teeth, one or more substituents R 5 C6-C selectively substituted with 18 aryl, and one or more substituents R 5 C2-C selectively substituted with 57Heteroaryl is selected from the group consisting of:
[0128] In one embodiment of the present invention, the organic molecule comprises or consists of the structure of formula II-1, where R 3 teeth, one or more substituents R 5 C6-C selectively substituted with 18 aryl, and one or more substituents R 5 C2-C selectively substituted with 57 Heteroaryl is selected from the group consisting of:
[0129] In one preferred embodiment of the present invention, the organic molecule comprises or consists of the structure of formula II-1, where R 3 is one or more substituents R 5 C6-C selectively substituted with 18 It is aryl.
[0130] In yet another preferred embodiment of the present invention, the organic molecule comprises or consists of the structure of formula II-1, where R 3 is one or more substituents R 6 C6-C selectively substituted with 18 It is aryl.
[0131] In a preferred embodiment, the organic molecule of the present invention comprises or consists of the structure of formula II-1, where R d and R e are linked together to form an aromatic ring system, and R V is N(R 5 )2 or one or more substituents R 2 ,R 3 ,R 5 and R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0132] In a preferred embodiment, the organic molecule of the present invention comprises or consists of the structure of formula II-1, where R d and R e are linked together to form an aromatic ring system, and R V is N(R 5 )2 or one or more adjacent substituents R 2 and adjacent substituent R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0133] In one preferred embodiment of the present invention, the organic molecule comprises or consists of the structure of formula II-1a:
[0134] [ka]
[0135] where R 3 is one or more substituents R 5 C6-C selectively substituted with 18 is aryl, Q1 is C and CR III is selected from the group consisting of Q 2 C and CR II is selected from the group consisting of Q 3 C and CR I is selected from the group consisting of Q4 is C and CR 1 is selected from the group consisting of Q 2 and Q 3 at least one substituent selected from the group consisting of is C; Q 2 and Q 3 When exactly one substituent selected from the group consisting of is C, Q 1 and Q 4Exactly one substituent selected from the group consisting of is C (the remainder are each CR III and CR 1 (It is).
[0136] This means that the structure of formula II-1a reinforces the following three structures of formula II-1aa, II-1ab, and II-1ac:
[0137] [ka] …II-1aa
[0138] [ka] …II-1ab
[0139] [ka] …II-1ac
[0140] In a further preferred embodiment of the invention, the organic molecule comprises or consists of the structure of formula II-1a: In this case, R 2 , R V and R IV At least one substituent selected from the group consisting of one or more substituents R 2 ,R V and R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0141] In a further preferred embodiment of the present invention, the organic molecule comprises or consists of a structure of formula II-1a, wherein at least one substituent R V is one or more adjacent substituents R 2 and adjacent substituent R IVtogether form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0142] In a further preferred embodiment of the present invention, the organic molecule comprises or consists of the structure of formula II-1a, wherein R 2 , R V and R IV At least one substituent selected from the group consisting of one or more substituents R 2 ,R V and R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system, said ring system being selected from the group consisting of:
[0143] [ka]
[0144] Here, each dotted line represents a binding site.
[0145] In a preferred embodiment, the binding sites are located adjacent to each other, i.e., R 2 Preferably, R V Together with R, they form a ring system. V is preferably R and / or R IV forms a ring system with R IV is preferably R V This means that it forms a ring system with
[0146] In a further preferred embodiment of the present invention, the organic molecule comprises or consists of the structure of formula II-1a, wherein R 2 , R V and R IV At least one substituent selected from the group consisting of one or more substituents R 2 ,R V and R IVtogether form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system, said ring system being selected from the group consisting of:
[0147] [ka]
[0148] Here, each dotted line represents a binding site.
[0149] In one particular embodiment of the present invention, the organic molecule comprises or consists of the structure of formula II-1a, wherein R 2 , R V and R IV At least one substituent selected from the group consisting of:
[0150] one or more substituents R 2 ,R V and R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system, said ring system being selected from the group consisting of:
[0151] [ka]
[0152] where X 1 is S, O or NR 5 is.
[0153] In yet another preferred embodiment of the present invention, the organic molecule comprises or consists of the structure of formula II-1a, wherein R 2 , R V and R IV At least one substituent selected from the group consisting of one or more substituents R 2 ,R V and R IVtogether form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system, said ring system being selected from the group consisting of:
[0154] [ka]
[0155] Here, each dotted line represents a binding site.
[0156] In one embodiment of the present invention, the organic molecule comprises or consists of the structure of formula II-1a, where R 2 , R V and R IV At least one substituent selected from the group consisting of one or more substituents R 2 ,R V and R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system, said ring system being selected from the group consisting of:
[0157] [ka]
[0158] Here, each dotted line represents a binding site.
[0159] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula II-1ac:
[0160] [ka]
[0161] In yet another embodiment, the organic molecule comprises or consists of the structure of formula II-1ab:
[0162] [ka]
[0163] In one embodiment of the present invention, the organic molecule comprises or consists of the structure of Formula IIa:
[0164] [ka]
[0165] where: R b are in each case, independently of one another, Hydrogen, deuterium, N(R 5 )2, OR 5 , Si(R 5 )3, B(OR 5 )2, OSO2R 5 , CF3, CN, F, Br, I, one or more substituents R 5 C1-C selectively substituted with 40 Alkyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C1-C selectively substituted with 40 Alkoxy, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR5 is selectively substituted with one or more substituents R 5 C1-C selectively substituted with 40 thioalkoxy, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C2-C selectively substituted with 40 alkenyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C2-C selectively substituted with 40 Alkynyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C6-C selectively substituted with 60 aryl, and one or more substituents R 5 C2-C selectively substituted with 57 It is also selected from the group consisting of heteroaryl. Other than that, the above definitions may also apply. In yet another embodiment of the present invention, R b are in each case, independently of one another, Hydrogen, deuterium, Me, i Pr, t Bu, CN, CF3, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t pyridinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3 and Ph; Me, i Pr, t carbazolyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3 and Ph; Me, i Pr, t triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; It is also selected from the group consisting of N(Ph)2.
[0166] In yet another embodiment of the present invention, R b are in each case, independently of one another, Me, i Pr, t Bu, CN, CF3, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, tpyridinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3 and Ph; Me, i Pr, t carbazolyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3 and Ph; Me, i Pr, t triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; It is also selected from the group consisting of N(Ph)2.
[0167] In one preferred embodiment, an organic molecule of the invention comprises or consists of a structure of Formula IIa, where X is NR 3 and R d and R e are linked together to form an aromatic ring system, and R V is N(R 5 )2 or one or more substituents R 2 ,R 3 ,R 5 , and R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0168] In one preferred embodiment of the present invention, the organic molecule comprises or consists of the structure of Formula III:
[0169] [ka]
[0170] where the substituent R a and R 5 are each independently one or more substituents R a and R 5 with which selectively form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system;
[0171] Substituent R 1 ,R 2 ,R 3 ,R 4 ,R 5 ,R I ,R II ,R III ,R IV ,R V are, independently of one another, one or more substituents R 1 ,R 2 ,R 3 ,R 4 ,R 5 ,R I ,R II ,R III ,R IV ,R V with the optionally forming a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0172] In one preferred embodiment, an organic molecule of the present invention comprises or consists of a structure of Formula III, where X is NR 3 and R V is N(R5)2 or one or more substituents R 2 ,R 3 ,R 5 and R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0173] In one preferred embodiment of the present invention, the organic molecule comprises or consists of the structure of formula III-1:
[0174] [ka]
[0175] where R 3 is one or more substituents R 6 C6-C selectively substituted with 60 It is aryl.
[0176] In a preferred embodiment, the organic molecule of the present invention comprises or consists of the structure of formula III-1, where R V is N(R 5 )2 or one or more substituents R 2 , R 3 , R 5 and / or R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0177] In one preferred embodiment of the present invention, the organic molecule comprises or consists of the structure of formula III-2:
[0178] [ka]
[0179] where R 3 is one or more substituents R 5 C6-C selectively substituted with 18 It is aryl.
[0180] In one preferred embodiment of the present invention, the organic molecule comprises or consists of the structure of formula III-2, where R 3 is one or more substituents R 6 C6-C selectively substituted with 18 is aryl, R V is one or more substituents R 5 C2-C selectively substituted with 17 heteroaryl, and N(R 5 )2.
[0181] In a preferred embodiment, an organic molecule of the present invention comprises or consists of the structure of formula III-2, where R V is N(R 5 )2 or one or more substituents R 2 ,R3 ,R 5 and R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0182] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula III-2, where R V is N(C6-C 18 aryl)2.
[0183] In one preferred embodiment of the present invention, the organic molecule comprises or consists of the structure of formula III-2a:
[0184] [ka] where: R 1 , R 2 , R I , R II , R III , R IV and R V At least one substituent selected from the group consisting of: one or more substituents R 1 ,R 2 ,R 3 ,R 4 ,R 5 ,R I ,R II ,R III ,R IV and R V together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system, said ring system being selected from the group consisting of:
[0185] [ka]
[0186] Here, each dotted line represents a binding site.
[0187] In one preferred embodiment of the present invention, the organic molecule comprises or consists of the structure of formula III-2a, where R 3 is one or more substituents R 5 C6-C selectively substituted with 18 is aryl, R 1 , R 2 , R I , R II , R III , R IV and R V At least one substituent selected from the group consisting of one or more substituents R 1 ,R 2 ,R 3 ,R 4 ,R 5 ,R I ,R II ,R III ,R IV and R V together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system, said ring system being selected from the group consisting of:
[0188] [ka]
[0189] Here, each dotted line represents a binding site.
[0190] In one preferred embodiment of the present invention, the organic molecule comprises or consists of the structure of formula III-2b:
[0191] [ka]
[0192] In a further preferred embodiment of the present invention, the organic molecule comprises or consists of the structure of formula III-2b, wherein: R 2 , R V and RIV At least one substituent selected from the group consisting of: one or more substituents R 2 ,R V and R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system, said ring system being selected from the group consisting of:
[0193] [ka] Here, each dotted line represents a binding site.
[0194] In an even more preferred embodiment of the present invention, the organic molecule comprises or consists of the structure of formula III-2b, wherein: R 2 , R V and R IV At least one substituent selected from the group consisting of: one or more substituents R 2 ,R V and R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system, said ring system being selected from the group consisting of:
[0195] [ka]
[0196] Here, each dotted line represents a binding site.
[0197] In one embodiment of the present invention, the organic molecule comprises or consists of the structure of formula III-2b, where R 2 , R V and R IV At least one substituent selected from the group consisting of one or more substituents R 2 ,R V and R IVtogether form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system, said ring system being selected from the group consisting of:
[0198] [ka]
[0199] Here, each dotted line represents a binding site.
[0200] In one embodiment of the present invention, the organic molecule / oligomer comprises or consists of the structure of Formula III-2b, wherein at least one R a is different from hydrogen.
[0201] In one preferred embodiment of the present invention, the organic molecule comprises or consists of the structure of formula III-2c:
[0202] [ka]
[0203] In a further preferred embodiment of the present invention, the organic molecule comprises or consists of the structure of formula III-2c, wherein R 2 , R V and R IV At least one substituent selected from the group consisting of one or more substituents R 2 ,R V and R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system, said ring system being selected from the group consisting of:
[0204] [ka]
[0205] Here, each dotted line represents a binding site.
[0206] In one preferred embodiment of the present invention, the organic molecule comprises or consists of the structure of formula III-2c, where R 2 , R V and R IV At least one substituent selected from the group consisting of one or more substituents R 2 ,R V and R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system, said ring system being selected from the group consisting of:
[0207] [ka]
[0208] Here, each dotted line represents a binding site.
[0209] In yet another preferred embodiment of the present invention, the organic molecule comprises or consists of the structure of formula III-2c, wherein R 2 , R V and R IV At least one substituent selected from the group consisting of one or more substituents R 2 ,R V and R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system, said ring system being selected from the group consisting of:
[0210] [ka]
[0211] Here, each dotted line represents a binding site.
[0212] In one embodiment of the present invention, the organic molecule comprises or consists of the structure of formula III-2c, wherein: R2 , R V and R IV At least one substituent selected from the group consisting of: one or more substituents R 2 ,R V and R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system, said ring system being selected from the group consisting of:
[0213] [ka]
[0214] Here, each dotted line represents a binding site.
[0215] In one embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula III-2c, wherein at least one R a is different from hydrogen.
[0216] In a preferred embodiment of the present invention, the organic molecule comprises or consists of the following structures of formula III-2d-I, III-2d-II, III-2d-III and III-2d-IV:
[0217] [ka] …III-2d-I
[0218] [ka] …III-2d-II
[0219] [ka] …III-2d-III
[0220] [ka] …III-2d-IV
[0221] In one embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula III-2d-I, formula III-2d-II, formula III-2d-III, and formula III-2d-IV, wherein at least one R a is different from hydrogen.
[0222] In one embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula III-2d-I, formula III-2d-II, formula III-2d-III, and formula III-2d-IV, wherein X 1 is O. In a further preferred embodiment of the present invention, the organic molecule comprises or consists of the structure of formula III-2d-III:
[0223] [ka]
[0224] In one embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula III-2d-III, wherein at least one R a is different from hydrogen.
[0225] In one embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula III-2d-III, where X 1 is O.
[0226] In a further preferred embodiment of the present invention, the organic molecule comprises or consists of the structure of formula III-2d-IIIa:
[0227] [ka]
[0228] In one embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula III-2d-IIIa, wherein at least one R a is different from hydrogen.
[0229] In one embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula III-2d-IIIa, where X 1 is O.
[0230] In a further preferred embodiment of the present invention, the organic molecule comprises or consists of the structure of formula III-2d-IIIb:
[0231] [ka]
[0232] In one embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula III-2d-IIIb, wherein at least one R a is different from hydrogen.
[0233] In one embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula III-2d-IIIb, where X 1 is O.
[0234] In one embodiment of the present invention, the organic molecule comprises or consists of the structure of formula III-2c-IIIc:
[0235] [ka]
[0236] In one embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of a structure of formula III-2d-IIIc, wherein at least one R a is different from hydrogen.
[0237] In one embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of a structure of formula III-2d-IIIc, where X 1 is O.
[0238] In yet another preferred embodiment of the present invention, the organic molecule comprises or consists of the structure of formula III-3, formula III-4, or formula III-5:
[0239] [ka]
[0240] [ka]
[0241] [ka]
[0242] In one embodiment, the organic molecule comprises or consists of a structure of formula III-3, formula III-4, or formula III-5, wherein R V teeth, OPh, CF3, CN, F, C1-C5 alkyl, wherein one or more hydrogen atoms are optionally replaced, independently of one another, by deuterium, CN, CF or F; C1-C5 alkoxy, wherein one or more hydrogen atoms are optionally replaced, independently of one another, by deuterium, CN, CF or F; C1-C5 thioalkoxy, wherein one or more hydrogen atoms are optionally replaced, independently of one another, by deuterium, CN, CF or F; C2-C5 alkenyl, wherein one or more hydrogen atoms are optionally replaced, independently of one another, by deuterium, CN, CF or F; C2-C5 alkynyl, wherein one or more hydrogen atoms are optionally replaced, independently of one another, by deuterium, CN, CF or F; C6-C optionally substituted with one or more C1-C5 alkyl substituents 18 aryl, C2-C optionally substituted with one or more C1-C5 alkyl substituents 17 heteroaryl, N(C6-C 18 aryl)2, N(C2-C 17 heteroaryl)2, and N(C2-C 17 Heteroaryl)(C6-C 18 aryl).
[0243] Different exemplary embodiments of Formula III are as follows:
[0244] [ka]
[0245] [ka]
[0246] where the substituent R a and R 5 are independently one or more substituents Ra and R 5 with which selectively form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system; Otherwise, any one of the above definitions may apply. Further examples of organic molecules are:
[0247] [ka]
[0248] [ka]
[0249] [ka]
[0250] [ka]
[0251] Here, any one of the above definitions may be applied. In one embodiment, R a and R 5 are in each case independently of one another hydrogen (H), methyl (Me), i-propyl (CH(CH3)2)( i Pr), t-butyl ( t Bu), phenyl (Ph), CN, CF 3and diphenylamine (NPh2).
[0252] In one preferred embodiment of the invention, the organic molecule comprises or consists of the structure of Formula IIIa:
[0253] [ka]
[0254] In one preferred embodiment, an organic molecule of the present invention comprises or consists of a structure of Formula IIIa, where X is NR 3 and R V is N(R 5 )2 or one or more substituents R 2 ,R 3 ,R 5 and R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0255] In a preferred embodiment of the present invention, the organic molecule comprises or consists of a structure selected from the group consisting of Formula IIIa-1 and Formula IIIa-2:
[0256] [ka]
[0257] [ka]
[0258] In a preferred embodiment, an organic molecule of the invention comprises or consists of a structure of formula IIIa-1 or formula IIIa-2, where X is NR 3 and R V is N(R 5 )2 or one or more substituents R 2 ,R3 ,R 5 and R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0259] In one preferred embodiment of the invention, the organic molecule comprises or consists of the structure of Formula IIIb:
[0260] [ka]
[0261] In a preferred embodiment, an organic molecule of the present invention comprises or consists of a structure of formula IIIb, where R V is N(R 5 )2 or one or more substituents R 2 ,R 3 ,R 5 and R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0262] In a preferred embodiment of the present invention, the organic molecule comprises or consists of a structure selected from the group consisting of Formula IIIb-1 and Formula IIIb-2:
[0263] [ka]
[0264] [ka]
[0265] In a preferred embodiment, an organic molecule of the present invention comprises or consists of a structure of formula IIIb-1 or formula IIIb-2, where R V is N(R 5)2 or one or more substituents R 2 ,R 3 ,R 5 and R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0266] In one preferred embodiment of the present invention, the organic molecule comprises or consists of the structure of Formula IIIc:
[0267] [ka]
[0268] In one preferred embodiment, an organic molecule of the present invention comprises or consists of a structure of formula IIIc, wherein X is NR 3 If R V is N(R 5 )2 or one or more substituents R 2 ,R 3 and R 5 together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0269] In a preferred embodiment of the present invention, the organic molecule comprises or consists of a structure selected from the group consisting of Formula IIIc-1 and Formula IIIc-2:
[0270] [ka]
[0271] [ka]
[0272] In a preferred embodiment, an organic molecule of the invention comprises or consists of a structure of formula IIIc-1 or formula IIIc-2, where X is NR3 and R V is N(R 5 )2 or one or more substituents R 2 ,R 3 and R 5 together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0273] In one preferred embodiment of the invention, the organic molecule comprises or consists of the structure of formula IIId:
[0274] [ka]
[0275] In one preferred embodiment, the organic molecule of the present invention comprises or consists of a structure of formula IIId, wherein R V is N(R 5 )2 or one or more substituents R 2 ,R 3 and R 5 together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0276] In a preferred embodiment of the present invention, the organic molecule comprises or consists of a structure selected from the group consisting of Formula IIId-1 and Formula IIId-2:
[0277] [ka]
[0278] [ka]
[0279] In one preferred embodiment, R V teeth, one or more substituents R 5C2-C selectively substituted with 17 heteroaryl, and N(R 5 )2.
[0280] In a preferred embodiment, the organic molecule of the present invention comprises or consists of a structure of formula IIId-1 or formula IIId-2, wherein R V is N(R 5 )2 or one or more substituents R 2 ,R 3 and R 5 together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0281] In one preferred embodiment of the present invention, the organic molecule comprises or consists of the structure of formula IIIe-0:
[0282] [ka]
[0283] Q 1 C and CR III is selected from the group consisting of Q 2 C and CR II is selected from the group consisting of Q 3 C and CR I is selected from the group consisting of Q 4 C and CR 1 is selected from the group consisting of Q 2 and Q 3 at least one substituent selected from the group consisting of is C; Q 2 and Q 3 When exactly one substituent selected from the group consisting of is C, Q 1 and Q 4Exactly one substituent selected from the group consisting of is C (the remainder are CR III or CR 1 (It is).
[0284] In one embodiment, an organic molecule of the present invention comprises or consists of a structure of formula IIIe-0, where R V is N(R 5 )2 or one or more substituents R 2 ,R 3 ,R 5 and R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0285] In one embodiment, an organic molecule of the present invention comprises or consists of a structure of formula IIIe-0, where R V is one or more substituents R 2 ,R 3 ,R 5 and R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0286] In one embodiment, an organic molecule of the present invention comprises or consists of a structure of formula IIIe-0, where R 1 , R 2 , R III , R IV and R V At least one substituent selected from the group consisting of one or more substituents R 1 ,R 2 ,R 3 ,R 4 ,R 5 ,R I ,R II ,R III ,R IV and R V together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0287] In one embodiment, an organic molecule of the present invention comprises or consists of a structure of formula IIIe-0, where R 3 are independent of each other, one or more substituents R 5 C6-C selectively substituted with 18 aryl, and one or more substituents R 5 C2-C selectively substituted with 17 It is also selected from the group consisting of heteroaryl.
[0288] In one embodiment, an organic molecule of the present invention comprises or consists of a structure of formula IIIe-0, where R 3 are independent of each other, one or more substituents R 5 C6-C selectively substituted with 18 It is also selected from the group consisting of aryl.
[0289] In one embodiment, an organic molecule of the present invention comprises or consists of a structure of formula IIIe-0, wherein Q 4 is CR 1 is.
[0290] In one embodiment, an organic molecule of the present invention comprises or consists of a structure of formula IIIe-0, wherein R a are in each case, independently of one another, hydrogen, deuterium, N(R 5 )2, OR 5 , SR 5 , Si(R 5 )3. B(OR 5 )2, B(R 5 )2, OSO2R 5 , CF3, CN, halogen, one or more substituents R 5 C1-C selectively substituted with 18 Alkyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C1-C selectively substituted with 18 Alkoxy, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C1-C selectively substituted with 18 thioalkoxy, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C2-C selectively substituted with 18 alkenyl, where one or more non-adjacent CH groups are R5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C2-C selectively substituted with 18 Alkynyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C6-C selectively substituted with 18 aryl, and one or more substituents R 5 C2-C selectively substituted with 17 It is also selected from the group consisting of heteroaryl.
[0291] In one embodiment, an organic molecule of the present invention comprises or consists of a structure of formula IIIe-0, wherein R a are in each case, independently of one another, hydrogen, deuterium, one or more substituents R 5 C1-C selectively substituted with 18 Alkyl, one or more substituents R 5 C6-C selectively substituted with 18 aryl, and one or more substituents R 5 C2-C selectively substituted with17 It is also selected from the group consisting of heteroaryl.
[0292] In one embodiment, an organic molecule of the present invention comprises or consists of a structure of formula IIIe-0, wherein R a are in each case, independently of one another, hydrogen, deuterium, one or more substituents R 5 C1-C selectively substituted with 18 It is also selected from the group consisting of alkyl.
[0293] In one embodiment, an organic molecule of the present invention comprises or consists of a structure of formula IIIe-0, wherein R 1 , R 2 , R 3 , R 4 , R I , R II , R III , R IV , R Vは、 Independently of each other, hydrogen, deuterium, N(R 5 )2, OR 5 , Si(R 5 )3. B(R 5 )2, CF3, CN, halogen, one or more substituents R 5 C1-C selectively substituted with 18 Alkyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5is selectively substituted with one or more substituents R 5 C6-C selectively substituted with 18 aryl, and one or more substituents R 5 C2-C selectively substituted with 17 heteroaryl; R 5 are in each case, independently of one another, Hydrogen, deuterium, N(R 6 )2, OR 6 , Si(R 6 )3, B(R 6 )2, CF3, CN, F, Br, I, one or more substituents R 6 C1-C selectively substituted with 18 Alkyl, where one or more non-adjacent CH groups are R 6 C=CR 6 , C≡C, Si(R 6 )2, Ge(R 6 )2, Sn(R 6 )2, C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO2, NR 6 , O, S or CONR 6 is selectively substituted with one or more substituents R 6 C6-C selectively substituted with 18 aryl, and one or more substituents R 6 C2-C selectively substituted with 17 heteroaryl; R 1 , R 2 , R 3 , R I , R II , R III , R IV , R 5 , R V are optionally joined together to form an aryl or heteroaryl ring optionally substituted with one or more C1-C5 alkyl substituents, deuterium, halogen, CN, or CF3.
[0294] In some embodiments, an organic molecule of the present invention comprises or consists of a structure of formula IIIe-0, where R 1 is not hydrogen, but R 1 is not deuterium.
[0295] In one embodiment, an organic molecule of the present invention comprises or consists of a structure of formula IIIe-0, wherein R 1 teeth, N(R 5 )2, OR 5 , Si(R 5 )3, B(OR 5 )2, B(R 5 )2, OSO2R 5 , CF3, CN, F, Br, I, one or more substituents R 5 C1-C selectively substituted with 40 Alkyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C1-C selectively substituted with 40 Alkoxy, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R5 C1-C selectively substituted with 40 thioalkoxy, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C2-C selectively substituted with 40 alkenyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C2-C selectively substituted with 40 Alkynyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C6-C selectively substituted with 60 aryl, and one or more substituents R 5 C2-C selectively substituted with57 heteroaryl;
[0296] The structure of formula IIIe-0 refers to the following three structures: formula IIIe-0a, formula IIIe, and formula IIIe-0b.
[0297] [ka]
[0298] In one embodiment of the present invention, the organic molecule comprises or consists of the structure of formula IIIe-0b:
[0299] [ka]
[0300] In one preferred embodiment of the present invention, the organic molecule comprises or consists of the structure of Formula IIIe:
[0301] [ka]
[0302] In one embodiment, an organic molecule of the invention comprises or consists of a structure of Formula IIIe, where R V is N(R 5 )2 or one or more substituents R 2 ,R 3 ,R 5 and R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0303] In one embodiment, an organic molecule of the invention comprises or consists of a structure of Formula IIIe, where R V is one or more substituents R 2 ,R 3 ,R5 and R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0304] In one embodiment, an organic molecule of the present invention comprises or consists of a structure of Formula IIIe, where R 1 , R 2 , R III , R IV and R V At least one substituent selected from the group consisting of one or more substituents R 1 ,R 2 ,R 3 ,R 4 ,R 5 ,R I ,R II ,R III ,R IV and R V together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0305] In one embodiment, an organic molecule of the invention comprises or consists of a structure of Formula IIIe, where R 3 are independent of each other, one or more substituents R 5 C6-C selectively substituted with 18 aryl, and one or more substituents R 5 C2-C selectively substituted with 17 It is also selected from the group consisting of heteroaryl.
[0306] In one embodiment, an organic molecule of the invention comprises or consists of a structure of Formula IIIe, where R 3 are independent of each other, one or more substituents R 5 C6-C selectively substituted with 18 It is also selected from the group consisting of aryl.
[0307] In one embodiment, an organic molecule of the present invention comprises or consists of a structure of Formula IIIe, wherein R a are in each case, independently of one another, hydrogen, deuterium, N(R 5 )2, OR 5 , SR 5 , Si(R 5 )3. B(OR 5 )2, B(R 5 )2, OSO2R 5 , CF3, CN, halogen, one or more substituents R 5 C1-C selectively substituted with 18 Alkyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C1-C selectively substituted with 18 Alkoxy, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C1-C selectively substituted with 18 thioalkoxy, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C2-C selectively substituted with 18 alkenyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C2-C selectively substituted with 18 Alkynyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C6-C selectively substituted with 18 aryl, and one or more substituents R 5C2-C selectively substituted with 17 It is also selected from the group consisting of heteroaryl.
[0308] In one embodiment, an organic molecule of the invention comprises or consists of a structure of Formula IIIe, wherein R a is, at each occurrence, independently of each other, hydrogen, deuterium, one or more substituents R 5 C1-C selectively substituted with 18 Alkyl, one or more substituents R 5 C6-C selectively substituted with 18 aryl, and one or more substituents R 5 C2-C selectively substituted with 17 It is also selected from the group consisting of heteroaryl.
[0309] In one embodiment, an organic molecule of the present invention comprises or consists of a structure of Formula IIIe, wherein R a are in each case, independently of one another, hydrogen, deuterium, one or more substituents R 5 C1-C selectively substituted with 18 It is also selected from the group consisting of alkyl.
[0310] In one embodiment, an organic molecule of the present invention comprises or consists of a structure of Formula IIIe, wherein R 1 , R 2 , R 3 , R 4 , R I , R II , R III , R IV and R Vは、 Independently of each other, hydrogen, deuterium, N(R 5 )2, OR 5 , Si(R 5 )3. B(R 5 )2, CF3, CN, halogen, one or more substituents R 5 C1-C selectively substituted with 18 Alkyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C6-C selectively substituted with 18 aryl, and one or more substituents R 5 C2-C selectively substituted with 17 heteroaryl; R 5 are in each case, independently of one another, Hydrogen, deuterium, N(R 6 )2, OR 6 , Si(R 6 )3, B(R 6 )2, CF3, CN, F, Br, I, one or more substituents R 6 C1-C selectively substituted with 18 Alkyl, where one or more non-adjacent CH groups are R 6 C=CR 6 , C≡C, Si(R 6 )2, Ge(R 6 )2, Sn(R 6 )2, C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO2, NR 6 , O, S or CONR 6 is selectively substituted with one or more substituents R 6 C6-C selectively substituted with 18 aryl, and one or more substituents R 6 C2-C selectively substituted with 17 heteroaryl; R 1 , R 2 , R 3 , R I , R II , R III , R IV , R 5 , R V are optionally joined together to form an aryl or heteroaryl ring optionally substituted with one or more C1-C5 alkyl substituents, deuterium, halogen, CN, or CF3.
[0311] In one preferred embodiment, the organic molecule of the present invention comprises or consists of a structure of Formula IIIe, where R 1 is not hydrogen, but R 1 is not deuterium.
[0312] In one preferred embodiment, the organic molecule of the present invention comprises or consists of a structure of formula IIIe, wherein R 1 teeth, N(R 5 )2, OR 5 , Si(R 5 )3, B(OR 5 )2, B(R 5 )2, OSO2R 5 , CF3, CN, F, Br, I, one or more substituents R 5 C1-C selectively substituted with 40 Alkyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C1-C selectively substituted with 40 Alkoxy, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C1-C selectively substituted with 40 thioalkoxy, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C2-C selectively substituted with 40 alkenyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C2-C selectively substituted with40 Alkynyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C6-C selectively substituted with 60 aryl, and one or more substituents R 5 C2-C selectively substituted with 57 heteroaryl;
[0313] In one preferred embodiment of the present invention, the organic molecule comprises or consists of the structure of formula IIIe-2:
[0314] [ka]
[0315] In one embodiment, an organic molecule of the invention comprises or consists of the structure of formula IIIe-2, where R V is N(R 5 )2 or one or more substituents R 2 ,R 3 ,R 5 and R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0316] In one embodiment, an organic molecule of the invention comprises or consists of the structure of formula IIIe-2, where R V is one or more substituents R 2 ,R 3 ,R5 and R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0317] In one embodiment, an organic molecule of the present invention comprises or consists of the structure of formula IIIe-2, wherein R 1 , R 2 , R III , R IV and R V At least one substituent selected from the group consisting of one or more substituents R 1 ,R 2 ,R 3 ,R 4 ,R 5 ,R I ,R II ,R III ,R IV and R V together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0318] In one embodiment, an organic molecule of the invention comprises or consists of the structure of formula IIIe-2, where R 3 are independent of each other, one or more substituents R 5 C6-C selectively substituted with 18 aryl, and one or more substituents R 5 C2-C selectively substituted with 17 It is also selected from the group consisting of heteroaryl.
[0319] In one embodiment, an organic molecule of the invention comprises or consists of the structure of formula IIIe-2, where R 3 are independent of each other, one or more substituents R 5 C6-C selectively substituted with 18 It is also selected from the group consisting of aryl.
[0320] In one embodiment, an organic molecule of the invention comprises or consists of the structure of formula IIIe-2, wherein R a are in each case, independently of one another, hydrogen, deuterium, N(R 5 )2, OR 5 , SR 5 , Si(R 5 )3. B(OR 5 )2, B(R 5 )2, OSO2R 5 , CF3, CN, halogen, one or more substituents R 5 C1-C selectively substituted with 18 Alkyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C1-C selectively substituted with 18 Alkoxy, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C1-C selectively substituted with 18 thioalkoxy, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C2-C selectively substituted with 18 alkenyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C2-C selectively substituted with 18 Alkynyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C6-C selectively substituted with 18 aryl, and one or more substituents R 5C2-C selectively substituted with 17 It is also selected from the group consisting of heteroaryl.
[0321] In one embodiment, an organic molecule of the invention comprises or consists of the structure of formula IIIe-2, wherein R a are in each case, independently of one another, hydrogen, deuterium, one or more substituents R 5 C1-C selectively substituted with 18 Alkyl, one or more substituents R 5 C6-C selectively substituted with 18 aryl, and one or more substituents R 5 C2-C selectively substituted with 17 It is also selected from the group consisting of heteroaryl.
[0322] In one embodiment, an organic molecule of the invention comprises or consists of the structure of formula IIIe-2, wherein R a are in each case, independently of one another, hydrogen, deuterium, one or more substituents R 5 C1-C selectively substituted with 18 It is also selected from the group consisting of alkyl.
[0323] In one embodiment, an organic molecule of the invention comprises or consists of the structure of formula IIIe-2, wherein R 1 , R 2 , R 3 , R 4 , R I , R II , R III , R IV and R Vは、 Independently of each other, hydrogen, deuterium, N(R 5 )2, OR 5 , Si(R5 )3. B(R 5 )2, CF3, CN, halogen, one or more substituents R 5 C1-C selectively substituted with 18 Alkyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C6-C selectively substituted with 18 aryl, and one or more substituents R 5 C2-C selectively substituted with 17 heteroaryl; R 5 are in each case, independently of one another, Hydrogen, deuterium, N(R 6 )2, OR 6 , Si(R 6 )3, B(R 6 )2, CF3, CN, F, Br, I, one or more substituents R 6 C1-C selectively substituted with 18 Alkyl, where one or more non-adjacent CH groups are R 6 C=CR 6 , C≡C, Si(R 6 )2, Ge(R 6 )2, Sn(R 6 )2, C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO2, NR 6 , O, S or CONR 6is selectively substituted with one or more substituents R 6 C6-C selectively substituted with 18 aryl, and C2-C optionally substituted with one or more substituents R6 17 heteroaryl; R 1 , R 2 , R 3 , R I , R II , R III , R IV , R 5 , R V can be optionally joined together to form an aryl or heteroaryl ring optionally substituted with one or more C1-C5 alkyl substituents, deuterium, halogen, CN, or CF3.
[0324] In one preferred embodiment of the present invention, the organic molecule comprises or consists of the structure of formula IIIe-3:
[0325] [ka]
[0326] In one preferred embodiment of the present invention, the organic molecule comprises or consists of the structure of formula IIIe-4:
[0327] [ka]
[0328] In one embodiment, an organic molecule of the invention comprises or consists of the structure of formula IIIe-4, where R V is N(R 5 )2 or one or more substituents R 2 ,R 3 ,R 5 and R IVtogether form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0329] In one embodiment, an organic molecule of the present invention comprises or consists of the structure of formula IIIe-4, wherein R V is one or more substituents R 2 ,R 3 ,R 5 , R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0330] In one embodiment, an organic molecule of the present invention comprises or consists of the structure of formula IIIe-4, wherein R 1 , R 2 , R III , R IV and R V At least one substituent selected from the group consisting of one or more substituents R 1 , R 2 , R 3 , R 4 , R I , R II , R III , R IV and R V together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0331] In one embodiment, an organic molecule of the invention comprises or consists of the structure of formula IIIe-4, where R 3 are independent of each other, one or more substituents R 5 C6-C selectively substituted with 18 aryl, and one or more substituents R 5 C2-C selectively substituted with 17 It is also selected from the group consisting of heteroaryl.
[0332] In one embodiment, an organic molecule of the invention comprises or consists of the structure of formula IIIe-4, where R 3 are independent of each other, one or more substituents R 5 C6-C selectively substituted with 18 It is also selected from the group consisting of aryl.
[0333] In one embodiment, an organic molecule of the present invention comprises or consists of the structure of formula IIIe-4, wherein R a are in each case, independently of one another, hydrogen, deuterium, N(R 5 )2, OR 5 , SR 5 , Si(R 5 )3. B(OR 5 )2, B(R 5 )2, OSO2R 5 , CF3, CN, halogen, one or more substituents R 5 C1-C selectively substituted with 18 Alkyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C1-C selectively substituted with 18 Alkoxy, where one or more non-adjacent CH groups are R 5 C=CR5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C1-C selectively substituted with 18 thioalkoxy, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C2-C selectively substituted with 18 alkenyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C2-C selectively substituted with 18 Alkynyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C6-C selectively substituted with 18 aryl, and one or more substituents R 5 C2-C selectively substituted with 17 It is also selected from the group consisting of heteroaryl.
[0334] In one embodiment, an organic molecule of the present invention comprises or consists of the structure of formula IIIe-4, wherein R a are in each case, independently of one another, hydrogen, deuterium, one or more substituents R 5 C1-C selectively substituted with 18 Alkyl, one or more substituents R 5 C6-C selectively substituted with 18 aryl, and one or more substituents R 5 C2-C selectively substituted with 17 It is also selected from the group consisting of heteroaryl.
[0335] In one embodiment, an organic molecule of the present invention comprises or consists of the structure of formula IIIe-4, wherein R a are in each case, independently of one another, hydrogen, deuterium, one or more substituents R 5 C1-C selectively substituted with 18 It is also selected from the group consisting of alkyl.
[0336] In one embodiment, an organic molecule of the present invention comprises or consists of the structure of formula IIIe-4, wherein R 1 , R 2 , R 3 , R 4 , RI , R II , R III , R IV , R V are independent of each other, hydrogen, deuterium, N(R 5 )2, OR 5 , Si(R 5 )3. B(R 5 )2, CF3, CN, halogen, one or more substituents R 5 C1-C selectively substituted with 18 Alkyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C6-C selectively substituted with 18 aryl, and one or more substituents R 5 C2-C selectively substituted with 17 heteroaryl; R 5 are in each case, independently of one another, Hydrogen, deuterium, N(R 6 )2, OR 6 , Si(R 6 )3, B(R 6 )2, CF3, CN, F, Br, I, one or more substituents R 6 C1-C selectively substituted with 18 Alkyl, where one or more non-adjacent CH groups are R6 C=CR 6 , C≡C, Si(R 6 )2, Ge(R 6 )2, Sn(R 6 )2, C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO2, NR 6 , O, S or CONR 6 is selectively substituted with one or more substituents R 6 C6-C selectively substituted with 18 aryl, and one or more substituents R 6 C2-C selectively substituted with 17 heteroaryl; R 1 , R 2 , R 3 , R I , R II , R III , R IV , R 5 , R V are optionally joined together to form an aryl or heteroaryl ring optionally substituted with one or more C1-C5 alkyl substituents, deuterium, halogen, CN, or CF3.
[0337] In one preferred embodiment, R 1 , R 2 , R 3 , R 4 , R I , R II , R III , R IV and R V At least one substituent selected from the group consisting of is different from hydrogen.
[0338] The present invention also provides organic molecules in oligomeric form for use as emitters in optoelectronic devices, such oligomers comprising or consisting of a plurality (i.e., 2, 3, 4, 5, or 6) of units of formula IV:
[0339] [ka]
[0340] The oligomer is a dimer to a hexamer (m is 2, 3, 4, 5 or 6), particularly a dimer to a trimer (m is 2 or 3), or preferably a dimer (m is 2). - in the form of a plurality of units, as shown in formula IV, - a plurality of units represented by formula IV are linked by a linking group selected from the group consisting of a single bond, a C1-C3 alkylene group, a phenylene or naphthylene group, an anthracene group, a pyrene or pyridine group, a pyrimidine group, or a triazine group;
[0341] - a plurality of units are linked together such that the ring a and / or ring b contained in the unit of formula I-AB can be shared with at least one other adjacent unit of the oligomer;
[0342] [ka]
[0343] - the oligomeric units are linked together such that ring a and / or ring b of one unit is fused to ring a and / or ring b of one adjacent unit of the oligomer; - a plurality of units are linked together such that ring a and / or ring b and / or ring c contained in the unit of formula I-ABC can be shared with at least one other adjacent unit of the oligomer,
[0344] [ka]
[0345] - the oligomeric units are linked together such that ring a and / or ring b and / or ring c of one unit is fused with ring a and / or ring b and / or ring c of one adjacent unit of the oligomer, Where ring b and ring c of one unit of an oligomer are shared by ring b and ring c of an adjacent oligomer, the direct bond between ring b and ring c is shared as shown in the exemplary structure below:
[0346] [ka] ;
[0347] The optional substituent R of the unit shown in formula IV a ,R d ,R e ,R IV ,R V ,R 2 ,R 1 ,R I ,R II ,R III ,R 3 or R 4 is an optional substituent R of the adjacent unit a ,R d ,R e ,R IV ,R V ,R 2 ,R 1 ,R I ,R II ,R III ,R 3 or R 4 to form an aryl or heteroaryl ring, optionally substituted with one or more C1-C5 alkyl substituents, Ph, deuterium, halogen, CN, or CF3, either through fusion, direct bonding, or by one or more C1-C5 alkyl substituents, Ph, deuterium, halogen, CN, or CF3; Two adjacent rings can share a bond.
[0348] Various examples include:
[0349] [ka]
[0350] In some embodiments of oligomers, some of the units shown in Formula VI (ring a and / or ring b and / or ring c) may be covalently linked by adjacent units, as shown by the following exemplary structure:
[0351] [ka]
[0352] [ka]
[0353] [ka]
[0354] Further examples of oligomers in the form of dimers (m is 2) according to the present invention are as follows:
[0355] [ka]
[0356] [ka]
[0357] [ka]
[0358] In one embodiment of the present invention, the oligomer comprises or consists of a structure selected from the following group:
[0359] [ka]
[0360] [ka]
[0361]
change
[0362]
change
[0363]
change
[0364]
change
[0365]
change
[0366]
change
[0367]
change
[0368]
change
[0369]
change
[0370]
change
[0371] [ka]
[0372] [ka]
[0373] [ka]
[0374] [ka]
[0375] In one embodiment of the present invention, the oligomer is a dimer (m=2) or a trimer (m=3), preferably a dimer. In one preferred embodiment, R 1 , R 2 , R 3 , R 4 , R I , R II , R III , R IV , R V are, independently of each other, hydrogen, deuterium, N(R 5 )2, OR 5 , Si(R 5 )3. B(R 5 )2, CF3, CN, halogen, one or more substituents R 5 C1-C selectively substituted with 18 Alkyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C6-C selectively substituted with 18 aryl, and one or more substituents R 5 C2-C selectively substituted with 17 heteroaryl; R 5 are in each case, independently of one another, Hydrogen, deuterium, N(R 6 )2, OR 6 , Si(R 6 )3, B(R 6 )2, CF3, CN, F, Br, I, one or more substituents R 6 C1-C selectively substituted with 18 Alkyl, where one or more non-adjacent CH groups are R 6 C=CR 6 , C≡C, Si(R 6 )2, Ge(R 6 )2, Sn(R 6 )2, C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO2, NR 6 , O, S or CONR 6 is selectively substituted with one or more substituents R 6 C6-C selectively substituted with 18 aryl, and one or more substituents R 6 C2-C selectively substituted with 17 heteroaryl; R 1 , R 2 , R 3 , R I , R II , R III , R IV , R5 , R V can be optionally joined together to form an aryl or heteroaryl ring optionally substituted with one or more C1-C5 alkyl substituents, deuterium, halogen, CN, or CF3. In one embodiment of the oligomer, R 1 , R 2 , R 3 , R 4 , R I , R II , R III , R IV , R V are independent of each other, hydrogen, deuterium, N(R 5 )2, OR 5 , Si(R 5 )3. B(R 5 )2, CF3, CN, halogen, one or more substituents R 5 C1-C selectively substituted with 18 Alkyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C6-C selectively substituted with 18 aryl, and one or more substituents R 5 C2-C selectively substituted with 17 heteroaryl; R 5 are in each case, independently of one another, Hydrogen, deuterium, N(R 6 )2, OR 6 , Si(R 6 )3, B(R 6 )2, CF3, CN, F, Br, I, one or more substituents R 6 C1-C selectively substituted with 18 Alkyl, where one or more non-adjacent CH groups are R 6 C=CR 6 , C≡C, Si(R 6 )2, Ge(R 6 )2, Sn(R 6 )2, C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO2, NR 6 , O, S or CONR 6 is selectively substituted with one or more substituents R 6 C6-C selectively substituted with 18 aryl, and one or more substituents R 6 C2-C selectively substituted with 17 heteroaryl; R located adjacent to each other 1 , R 2 , R I , R II , R III , R IV , R 5 , R V are optionally joined together to form an aryl or heteroaryl ring optionally substituted with one or more C1-C5 alkyl substituents, deuterium, halogen, CN, or CF3. In one embodiment of the oligomer, R 1 , R 2 , R 3 , R 4 , R I , R II , R III , R IV , R V , R a are independent of each other, hydrogen, deuterium, N(R 5 )2, OR 5 , SR 5 , Si(R 5 )3. B(OR 5 )2, B(R 5 )2, OSO2R 5 , CF3, CN, halogen, one or more substituents R 5 C1-C selectively substituted with 18 Alkyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C1-C selectively substituted with 18 Alkoxy, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C1-C selectively substituted with 18 thioalkoxy, where one or more non-adjacent CH groups are R 5 C=CR5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C2-C selectively substituted with 18 alkenyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C2-C selectively substituted with 18 Alkynyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C6-C selectively substituted with 18 aryl, and one or more substituents R 5 C2-C selectively substituted with 17 heteroaryl; R 5 are in each case, independently of one another, Hydrogen, deuterium, N(R 6 )2, OR 6 , Si(R 6 )3, B(OR 6 )2, B(R 6 )2, OSO2R 6 , CF3, CN, F, Br, I, one or more substituents R 6 C1-C selectively substituted with 18 Alkyl, where one or more non-adjacent CH groups are R 6 C=CR 6 , C≡C, Si(R 6 )2, Ge(R 6 )2, Sn(R 6 )2, C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO2, NR 6 , O, S or CONR 6 is selectively substituted with one or more substituents R 6 C1-C selectively substituted with 18 Alkoxy, where one or more non-adjacent CH groups are R 6 C=CR 6 , C≡C, Si(R 6 )2, Ge(R 6 )2, Sn(R 6 )2, C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO2, NR 6 , O, S or CONR 6 is selectively substituted with one or more substituents R 6 C1-C selectively substituted with 18 thioalkoxy, where one or more non-adjacent CH groups are R 6 C=CR 6 , C≡C, Si(R 6 )2, Ge(R 6 )2, Sn(R 6 )2, C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO2, NR6 , O, S or CONR 6 is selectively substituted with one or more substituents R 6 C2-C selectively substituted with 18 alkenyl, where one or more non-adjacent CH groups are R 6 C=CR 6 , C≡C, Si(R 6 )2, Ge(R 6 )2, Sn(R 6 )2, C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO2, NR 6 , O, S or CONR 6 is selectively substituted with one or more substituents R 6 C2-C selectively substituted with 18 Alkynyl, where one or more non-adjacent CH groups are R 6 C=CR 6 , C≡C, Si(R 6 )2, Ge(R 6 )2, Sn(R 6 )2, C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO2, NR 6 , O, S or CONR 6 is selectively substituted with one or more substituents R 6 C6-C selectively substituted with 18 aryl, and one or more substituents R 6 C2-C selectively substituted with 17 heteroaryl; Substituent R a ,R d ,R e ,R 5 are each independently one or more substituents R a ,R d ,R e ,R 5with which selectively form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system; Substituent R 1 ,R 2 ,R 3 ,R 4 ,R 5 ,R I ,R II ,R III ,R IV ,R V are, independently of one another, one or more substituents R 1 ,R 2 ,R 3 ,R 4 ,R 5 ,R I ,R II ,R III ,R IV ,R V with the optionally forming a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0376] In one embodiment of the present invention, the organic molecule is comprised of a dimer or trimer, where R 1 , R 2 , R a ,R d ,R e ,R I , R II , R III , R IV and R V are in each case, independently of one another, hydrogen, Me, i Pr 、 t Bu 、 CN, CF3, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, tpyridinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3 and Ph; Me, i Pr, t pyrimidinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3 and Ph; Me, i Pr, t carbazolyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3 and Ph; Me, i Pr, t triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; It is also selected from the group consisting of N(Ph)2. In one embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of Formula IV, wherein at least one R a is different from hydrogen.
[0377] In one preferred embodiment, an organic molecule of the present invention comprises or consists of the structure of formula IV, where X is NR 3 and R d and R e are linked together to form an aromatic ring system, and R V is N(R 5 )2 or one or more substituents R 2 ,R 3 ,R 5 and R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0378] In one preferred embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula IV, where X, in each occurrence, independently of each other, is a direct bond, NR 3 , C.R. 3 R 4, S and O.
[0379] In a further preferred embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula IV, where X, in each occurrence, independently of each other, is a direct bond, NR 3 , S and O.
[0380] In one embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of Formula IV, where X, in each occurrence, independently, is a direct bond and NR 3 is selected from the group consisting of:
[0381] In one embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of Formula IV, where X is NR 3 is.
[0382] In one preferred embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of Formula IV, where R 3 are independent of each other, one or more substituents R 5 C1-C selectively substituted with 40 Alkyl, one or more substituents R 5 C6-C selectively substituted with 18 aryl, and one or more substituents R 5 C2-C selectively substituted with 17 It is also selected from the group consisting of heteroaryl.
[0383] In one preferred embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of Formula IV, where R V are in each case, independently of one another, N(R 5 )2, OR 5 , one or more substituents R 5C1-C selectively substituted with 18 Alkyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C6-C selectively substituted with 18 aryl, and C2-C 17 heteroaryl; R V are, independently of each other, monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzofused ring systems optionally substituted with one or more C1-C5 alkyl substituents, deuterium, halogen, CN, or CF3, and are substituted with one or more substituents R 2 and R IV At the same time, it is selectively formed.
[0384] In a preferred embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of Formula IVa-0, Formula IVb-0:
[0385] [ka]
[0386] [ka]
[0387] In one embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of Formula IVa, Formula IVb-0:
[0388] [ka]
[0389] [ka]
[0390] In one embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of Formula IVa, Formula IVb-0, wherein at least one R 5 is different from hydrogen.
[0391] In a preferred embodiment, the organic molecule of the present invention comprises or consists of the structure of formula IVa, formula IVb-0, where X is NR 3 and R d and R e are linked together to form an aromatic ring system, and R V is N(R 5 )2 or one or more substituents R 2 ,R 3 ,R 5 ,R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system. In a preferred embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula IVa, formula IVb-0, where X, in each occurrence, independently of each other, is a direct bond, NR 3 , C.R. 3 R 4 , S and O.
[0392] In a further preferred embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of a structure of formula IVa, formula IVb-0, where X, in each occurrence, independently of each other, is a direct bond, NR 3 , S and O.
[0393] In one embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of Formula IVa, Formula IVb-0, where X, in each occurrence, independently, is a direct bond and NR 3 is selected from the group consisting of:
[0394] In one embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of Formula IVa, Formula IVb-0, where X is NR 3 is.
[0395] In a preferred embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of Formula IVa, Formula IVb-0, where R 3 are independent of each other, one or more substituents R 5 C1-C selectively substituted with 40 Alkyl, one or more substituents R 5 C6-C selectively substituted with 18 aryl, and one or more substituents R 5 C2-C selectively substituted with 17 It is also selected from the group consisting of heteroaryl.
[0396] In a preferred embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of Formula IVa, Formula IVb-0, where R V are in each case, independently of one another, N(R 5 )2, OR 5 , one or more substituents R 5 C1-C selectively substituted with 18 Alkyl, where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 is selectively substituted with one or more substituents R 5 C6-C selectively substituted with 18 aryl, and C2-C 17 heteroaryl; R V are, independently of one another, one or more substituents R 2 and R IV together optionally form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system optionally substituted with one or more C1-C5 alkyl substituents, deuterium, halogen, CN, or CF3.
[0397] In one embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula IVa-0:
[0398] [ka]
[0399] In one preferred embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of Formula IVa:
[0400] [ka]
[0401] In one embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula IVa-2:
[0402] [ka]
[0403] In one embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula IVa-3:
[0404] [ka]
[0405] In one embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula IVa-4:
[0406] [ka]
[0407] In one preferred embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula IVb-0:
[0408] [ka]
[0409] In one embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula IVb-0, wherein at least one R a is different from hydrogen.
[0410] In one preferred embodiment, an organic molecule of the present invention comprises or consists of a structure of formula IVb-0, where X is NR 3 and R d and R e are linked together to form an aromatic ring system, and R V is N(R 5 )2 or one or more substituents R 2 ,R 3 ,R 5 and R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0411] In one preferred embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula IVb-0, where X, in each occurrence, independently of each other, is a direct bond, NR 3 , C.R. 3 R 4 , S and O.
[0412] In a further preferred embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula IVb-0, where X, in each occurrence, independently of each other, is a direct bond, NR 3 , S and O.
[0413] In one embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula IVb-0, where X, in each occurrence, independently, is a direct bond and NR 3 is selected from the group consisting of:
[0414] In one embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula IVb-0, where X is NR 3 is.
[0415] In a further preferred embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula IVb-0a:
[0416] [ka]
[0417] In one embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula IVb-0a, wherein at least one R a is different from hydrogen.
[0418] In one preferred embodiment, an organic molecule of the present invention comprises or consists of a structure of formula IVb-0a, where X is NR 3 and R d and R e are linked together to form an aromatic ring system, and R V is N(R 5 )2 or one or more substituents R 2 ,R 3 ,R 5 and R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0419] In one preferred embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula IVb-0a, where X, in each occurrence, independently of each other, is a direct bond, NR 3 , C.R. 3 R 4 , S and O.
[0420] In a further preferred embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of a structure of formula IVb-0a, where X, in each occurrence, independently of each other, is a direct bond, NR 3 , S and O.
[0421] In one embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of a structure of formula IVb-0a, where X, in each occurrence, independently, is a direct bond and NR 3 is selected from the group consisting of:
[0422] In one embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula IVb-0a, where X is NR 3 is.
[0423] In one preferred embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula IVb-0b:
[0424] [ka]
[0425] In one embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula IVb-0b, wherein at least one R a is different from hydrogen.
[0426] In one preferred embodiment, the organic light-emitting molecule of the present invention comprises or consists of a structure of formula IVb-0b, where X is NR 3 and R V is N(R 5 )2 or one or more substituents R 2 ,R 3 ,R 5 and R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0427] In one preferred embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of a structure of formula IVb-0b, where X, in each occurrence, independently of each other, is a direct bond, NR 3 , C.R. 3 R 4 , S and O.
[0428] In a further preferred embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of a structure of formula IVb-0b, where X, in each occurrence, independently of each other, is a direct bond, NR 3 , S and O.
[0429] In one embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula IVb-0b, where X, in each occurrence, independently, is a direct bond and NR 3 is selected from the group consisting of:
[0430] In one embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula IVb-0b, where X is NR 3 is.
[0431] In a further preferred embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula IVb-0c: [ka]
[0432] In one embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula IVb-0c, wherein at least one R a is different from hydrogen.
[0433] In one preferred embodiment, the organic light-emitting molecule of the present invention comprises or consists of a structure of formula IVb-0c, where X is NR 3 and R V is N(R 5 )2 or one or more substituents R 2 ,R 3 ,R 5 and R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0434] In one preferred embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of a structure of formula IVb-0c, where X, in each occurrence, independently of each other, is a direct bond, NR 3 , C.R. 3 R 4 , S and O.
[0435] In a further preferred embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of a structure of formula IVb-0c, where X, in each occurrence, independently of each other, is a direct bond, NR 3 , S and O.
[0436] In one embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of a structure of formula IVb-0c, where X, in each occurrence, independently, is a direct bond and NR 3 is selected from the group consisting of:
[0437] In one embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula IVb-0c, where X is NR 3 is.
[0438] In one preferred embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of Formula IVb:
[0439] [ka]
[0440] In one preferred embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula IVb-2:
[0441] [ka]
[0442] In one preferred embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula IVb-3:
[0443] [ka]
[0444] In one embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula IVb-3, wherein at least one R a is different from hydrogen.
[0445] In a preferred embodiment, the organic molecule of the present invention comprises or consists of the structure of formula IVb-3, where R V is N(R 5 )2 or one or more substituents R 2 ,R 3 ,R 5 and R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0446] In one preferred embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula IVb-4:
[0447] [ka]
[0448] In one embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula IVb-4, wherein at least one R a is different from hydrogen.
[0449] In a preferred embodiment, the organic molecule of the present invention comprises or consists of the structure of formula IVb-3, where R V is N(R 5 )2 or one or more substituents R 2 ,R 3 ,R 5 and R IV together form a monocyclic or polycyclic, aliphatic, aromatic, heteroaromatic, and / or benzo-fused ring system.
[0450] In one embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of Formula IVc:
[0451] [ka]
[0452] In one embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula IVc-2:
[0453] [ka]
[0454] In one embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula IVd:
[0455] [ka]
[0456] In one preferred embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula IVd-2:
[0457] [ka] In one embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of Formula IVe:
[0458] [ka]
[0459] In one preferred embodiment of the present invention, the organic molecule / oligopolymer comprises or consists of the structure of formula IVe-2:
[0460] [ka]
[0461] As used herein, "aryl" and "aromatic" may be understood in the broadest sense as any monocyclic, bicyclic, or polycyclic aromatic moiety. Thus, an aryl group contains 6 to 60 aromatic ring atoms, and a heteroaryl group contains 5 to 60 aromatic ring atoms, at least one of which is a heteroatom. However, the number of aromatic ring atoms may also be given herein by the subscript number in the definition of a specific substituent. In particular, a heteroaromatic ring contains 1 to 3 heteroatoms. As used herein, "heteroaryl" and "heteroaromatic" may be understood in the broadest sense as any monocyclic, bicyclic, or polycyclic heteroaromatic moiety containing at least one heteroatom. The heteroatoms, in each case, may be identical or different and may be independently selected from the group consisting of N, O, and S. Thus, "arylene" refers to a divalent substituent that possesses two binding sites to other molecular structures and serves as a linker structure. In some exemplary embodiments, if a "group" is defined differently from the definitions given herein, e.g., if the number of aromatic ring atoms or the number of heteroatoms differs from the definitions given, the definition in the exemplary embodiment applies. According to the present invention, a fused (cyclic) aromatic or fused (cyclic) heteroaromatic polycycle is composed of two or more single aromatic or heteroaromatic rings that form the polycycle via a condensation reaction.
[0462] In particular, in this specification, the term "aryl group or heteroaryl group" refers to a group that can be bonded via any one position of an aromatic group or heteroaromatic group, specifically, benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, fluoranthene, benzanthracene, benzphenanthrene, tetracene, pentacene, benzpyrene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthoyl midazole, phenanthroimidazole, pyridoimidazole, pyrazinoimidazole, quinoxalinoimidazole, oxazole, benzoxazole, naphthoxazole, anthroxazole, phenanthroxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, 1,3,5-triazine, quinoxaline, pyrazine, phenazine, naphthyridine, carboline, benzocarboline, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,2,3,4-tetrazine, purine, pteridine, indolizine and benzothiadiazole, or groups derived from combinations of the foregoing groups.
[0463] In this specification, a "cyclic group" may be understood in the broadest sense as any monocyclic, bicyclic or polycyclic moiety.
[0464] As used herein, "biphenyl" as a substituent is understood in its broadest sense as ortho-biphenyl, meta-biphenyl, or para-biphenyl, where ortho, meta, and para are defined in relation to the point of attachment to another chemical entity.
[0465] As used herein, "alkyl group" may be understood in the broadest sense as any linear, branched, or cyclic alkyl substituent. In particular, "alkyl" includes the substituents methyl (Me), ethyl (Et), n-propyl (nPr), i-propyl ( i Pr), cyclopropyl, n-butyl ( n Bu), i-butyl ( i Bu), s-butyl ( s Bu), t-butyl ( t Bu), cyclobutyl, 2-methylbutyl, n-pentyl, s-pentyl, t-pentyl, 2-pentyl, neo-pentyl, cyclopentyl, n-hexyl, s-hexyl, t-hexyl, 2-hexyl, 3-hexyl, neo-hexyl, cyclohexyl, 1-methylcyclopentyl, 2-methylpentyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, cycloheptyl, 1-methylcyclo Hexyl, n-octyl, 2-ethylhexyl, cyclooctyl, 1-bicyclo[2,2,2]octyl, 2-bicyclo[2,2,2]-octyl, 2-(2,6-dimethyl)octyl, 3-(3,7-dimethyl)octyl, adamantyl, 2,2,2-trifluoroethyl, 1,1-dimethyl-n-hex-1-yl, 1,1-dimethyl-n-hept-1-yl, 1,1-dimethyl-n-oct-1-yl, 1, 1-dimethyl-n-dec-1-yl, 1,1-dimethyl-n-dodec-1-yl, 1,1-dimethyl-n-tetradec-1-yl, 1,1-dimethyl-n-hexadec-1-yl, 1,1-dimethyl-n-octadec-1-yl, 1,1-diethyl-n-hex-1-yl, 1,1-diethyl-n-hept-1-yl, 1,1-diethyl-n-oct-1-yl, 1,1-diethyl-n-dec-1-yl, 1,1-diethyl-n 1-(n-propyl)-cyclohex-1-yl, 1-(n-butyl)-cyclohex-1-yl, 1-(n-hexyl)-cyclohex-1-yl, 1-(n-octyl)-cyclohex-1-yl, and 1-(n-decyl)-cyclohex-1-yl.
[0466] As used herein, "alkenyl" includes linear, branched, and cyclic alkenyl substituents. "Alkenyl groups" include, for example, the substituents ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, or cyclooctadienyl.
[0467] As used herein, "alkynyl" includes linear, branched and cyclic alkynyl substituents. "Alkynyl groups" include, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl.
[0468] As used herein, "alkoxy" includes linear, branched, and cyclic alkoxy substituents. Exemplary "alkoxy groups" include methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, and 2-methylbutoxy.
[0469] As used herein, "thioalkoxy" includes linear, branched and cyclic thioalkoxy substituents, where the O in the exemplary alkoxy group is replaced with an S.
[0470] In this specification, "halogen" and "halo" may be understood in the broadest sense, preferably to mean fluorine, chlorine, bromine or iodine.
[0471] In this specification, whenever hydrogen (H) is mentioned, it is also replaced in each case by deuterium.
[0472] When a molecular fragment is described as being a substituent or attached to another moiety, it may be named as either the fragment (e.g., naphthyl, dibenzofuryl) or as the whole molecule (e.g., naphthalene, dibenzofuran). As used herein, such different ways of designating the substituent or attached fragment are considered equivalent.
[0473] In one embodiment, the organic molecule according to the present invention has an excited-state lifetime of 5.0 μs or less, 2.5 μs or less, specifically 2.0 μs or less, preferably 1.0 μs or less, or 0.7 μs or less, in a poly(methyl methacrylate) (PMMA) film containing 1 wt % to 5 wt %, specifically 2 wt %, of the organic molecule at room temperature.
[0474] In yet another embodiment of the present invention, the organic molecule according to the present invention has an emission peak in the visible or near-ultraviolet range, i.e., in the wavelength range of 380 nm to 800 nm, at room temperature in a poly(methyl methacrylate) (PMMA) film containing 1 wt % to 5 wt %, specifically 2 wt %, of the organic molecule, with a full width at half maximum of less than 0.25 eV, preferably less than 0.22 eV, more preferably less than 0.18 eV, and even more preferably less than 0.15 eV or less than 0.12 eV.
[0475] Orbital energies and excited state energies are also determined through experimental methods. The energy of the highest occupied molecular orbital, E HOMO is determined from cyclic voltammetry measurements by methods known to those skilled in the art, which have an accuracy of 0.1 eV. The energy of the lowest unoccupied molecular orbital, E LUMO is E HOMO +E gap where E gap is determined as follows: for the host compound, unless otherwise specified, the onset of the emission spectrum of a poly(methyl methacrylate) (PMMA) film containing 10 wt % of the host is E gap For the emitter molecule, E gap is determined as the energy at which the excitation and emission spectra of a PMMA film having 1 wt% to 5 wt%, specifically 2 wt%, of the emitter intersect. For the organic molecules according to the present invention, E gap is determined as the energy at which the excitation spectrum and emission spectrum of a PMMA film containing 1 wt% to 5 wt%, specifically 2 wt%, of the emitter intersect.
[0476] The energy of the first excited triplet state T1 is determined from the onset of the emission spectrum at low temperatures, typically 77 K. For host compounds where the first excited singlet state and the lowest triplet state are energetically separated by >0.4 eV, phosphorescence can generally be seen as a normal-state spectrum in 2-Me-THF. Thus, triplet energies are also determined from the onset of the phosphorescence spectrum. For TADF emitter molecules, the energy of the first excited triplet state T1 is determined from the onset of the delayed emission spectrum at 77 K, and unless otherwise specified, is measured on a PMMA film containing 1 wt% to 5 wt%, specifically 2 wt%, of the emitter. For organic molecules according to the present invention, the energy is measured on a PMMA film containing 1 wt% to 5 wt%, specifically 2 wt%, of the organic molecule according to the present invention. For both the host compound and the emitter compound, the energy of the first excited singlet state S1 is determined from the onset of the emission spectrum measured on a PMMA film containing 10 wt % of the host compound or emitter compound, unless otherwise specified, and in the case of the organic molecule according to the present invention, it is determined from the onset of the emission spectrum measured on a PMMA film containing 1 wt % to 5 wt %, specifically 2 wt %, of the organic molecule according to the present invention.
[0477] The onset of the emission spectrum is determined by calculating the intersection of a tangent to the emission spectrum with the x-axis, the tangent to the emission spectrum being set at the high energy side of the emission band and the half maximum point of the maximum intensity of the emission spectrum.
[0478] Yet another aspect of the present invention relates to the use of the organic molecules of the present invention as light emitters or absorbers, and / or host materials, and / or electron transport materials, and / or hole injection materials, and / or hole blocking materials in optoelectronic devices.
[0479] A preferred embodiment relates to the use of organic molecules according to the invention as light emitters in optoelectronic devices.
[0480] In the broadest sense, the optoelectronic component is understood to be any component based on organic materials suitable for emitting light in the visible or near ultraviolet (UV) range, i.e., in the wavelength range from 380 nm to 800 nm. Preferably, the optoelectronic component is capable of emitting light in the visible range, i.e., from 400 nm to 800 nm.
[0481] In connection with such applications, the optoelectronic element is more particularly selected from the group consisting of:
[0482] Organic light-emitting diodes (OLEDs), Light-emitting electrochemical cells, OLED sensors (specifically gas and vapor sensors that are not completely shielded from the surrounding environment), organic diodes, ·Organic solar cells, Organic transistors, Organic field-effect transistors, Organic lasers, Down-conversion element.
[0483] In connection with such applications, in a preferred embodiment, the optoelectronic device is selected from the group consisting of an organic light emitting diode (OLED), a light emitting electrochemical cell (LEC), and a light emitting transistor.
[0484] When the organic molecules according to the present invention are used, the proportion of the organic molecules according to the present invention in the light-emitting layer of the optoelectronic device, specifically the OLED, is 0.1 wt% to 99 wt%, specifically 1 wt% to 80 wt%. In another embodiment, the proportion of the organic molecules in the light-emitting layer is 100 wt%.
[0485] In one embodiment, the emissive layer comprises not only an organic molecule according to the present invention but also a host material whose triplet (T1) energy level and singlet (S1) energy level are energetically higher than the triplet (T1) energy level and singlet (S1) energy level, respectively, of the organic molecule.
[0486] Yet another aspect of the present invention relates to a composition comprising or consisting of: (a) one or more organic molecules according to the invention, in particular in emitter and / or host form, (b) one or more emitter and / or host materials different from the organic molecules according to the present invention, and (c) optionally one or more dyes and / or one or more solvents;
[0487] In one embodiment, the light-emitting layer comprises a composition comprising (or consisting essentially of) or consisting of: (a) one or more organic molecules according to the invention, in particular in emitter and / or host form, (b) one or more emitter and / or host materials different from the organic molecules according to the present invention, and (c) optionally one or more dyes and / or one or more solvents.
[0488] In a specific embodiment, the emissive layer EML comprises a composition comprising (or consisting essentially of) or consisting of: (i) 0.1 wt % to 10 wt %, preferably 0.5 wt % to 5 wt %, specifically 1 wt % to 3 wt % of one or more organic molecules according to the present invention. E (ii) 5 wt% to 99 wt%, preferably 15 wt% to 85 wt%, specifically 20 wt% to 75 wt% of one or more host compounds H (iii) 0.9 wt% to 94.9 wt%, preferably 14.5 wt% to 80 wt%, in particular 24 wt% to 77 wt% of at least one additional host compound D having a structure different from that of the molecule according to the invention; (iv) optionally, 0 wt % to 94 wt %, preferably 0 wt % to 65 wt %, specifically 0 wt % to 50 wt % of a solvent; and (v) optionally, 0 wt% to 30 wt%, in particular 0 wt% to 20 wt%, preferably 0 wt% to 5 wt% of at least one additional emitter molecule F having a structure different from that of the molecule according to the present invention;
[0489] Preferably, energy can be transferred from the host compound H to one or more organic molecules according to the present invention, in particular from the first excited triplet state T1(H) of the host compound H to the first excited triplet state T1(E) of one or more organic molecules according to the present invention, and / or from the first excited singlet state S1(H) of compound H to the first excited singlet state S1(E) of one or more organic molecules according to the present invention.
[0490] In one embodiment, the host compound H has an energy E in the range of −5 eV to 6.5 eV. HOMO (H) having a highest occupied molecular orbital HOMO(H), and one or more additional host compounds D have an energy E HOMO (D) has a highest occupied molecular orbital HOMO(D), where E HOMO (H)>E HOMO (D).
[0491] In another embodiment, the host compound H has an energy E LUMO (H) having a lowest unoccupied molecular orbital LUMO(H) with energy E LUMO (D) has a lowest unoccupied molecular orbital LUMO(D), where E LUMO (H)>E LUMO (D).
[0492] In one embodiment, the host compound H has an energy E HOMO (H) with the highest occupied molecular orbital HOMO(H), and energy E LUMO (H) having a lowest unoccupied molecular orbital LUMO(H),
[0493] One or more additional host compounds D may have an energy E HOMO (D) with highest occupied molecular orbital HOMO(D), and energy E LUMO (D) has a lowest unoccupied molecular orbital LUMO (D), The organic molecule E according to the present invention has an energy E HOMO (E) highest occupied molecular orbital HOMO (E), and energy E LUMO (E) lowest unoccupied molecular orbital LUMO (E), where: E HOMO (H)>E HOMO (D), and the energy level of the highest occupied molecular orbital HOMO (E) of the organic molecule E according to the present invention (E HOMO (E)) and the energy level of the highest occupied molecular orbital (HOMO) of the host compound H (E HOMO (H)) is −0.5 eV to 0.5 eV, preferably −0.3 eV to 0.3 eV, more preferably −0.2 eV to 0.2 eV, or −0.1 eV to 0.1 eV, E LUMO (H)> ELUMO (D), and the energy level E (E LUMO (E)) and the energy level D(E) of the lowest unoccupied molecular orbital LUMO(D) of one or more additional host compounds D. LUMO The difference from (D)) is −0.5 eV to 0.5 eV, preferably −0.3 eV to 0.3 eV, and more preferably −0.2 eV to 0.2 eV, or −0.1 eV to 0.1 eV.
[0494] In one embodiment of the present invention, the host compound D and / or the host compound H is a thermally activated The TADF material has an energy difference ΔE between the first excited singlet state (S1) and the first excited triplet state (T1). ST The value is 2,500 cm -1 The TADF material preferably has a wavelength of less than 3,000 cm -1 Less than, preferably, 1,500 cm -1less than, more preferably, 1,000 cm -1 Less than or equal to 500cm -1 Less than ΔE ST Indicates the value. In one embodiment, host compound D is a TADF material and host compound H is a TADF material having a wavelength of 2,500 cm -1 Excessive ΔE ST In a specific embodiment, the host compound D is a TADF material and the host compound H is CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole 、9 -[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole, and 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole.
[0495] In one embodiment, the host compound H is a TADF material and the host compound D is a TADF material having a wavelength of 2,500 cm -1 In a specific embodiment, the host compound H is a TADF material, and the host compound D is selected from the group consisting of 2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine (T2T), 2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine (T3T), and / or 2,4,6-tris(9,9'-spirobifluoren-2-yl)-1,3,5-triazine (TST).
[0496] In yet another aspect, the present invention relates to an optoelectronic device comprising an organic molecule or composition of the type described herein, and more particularly to a device having a form selected from the group consisting of an organic light-emitting diode (OLED), a light-emitting electrochemical cell, an OLED sensor (e.g., an open-circuit gas sensor or vapor sensor), an organic diode, an organic solar cell, an organic transistor, an organic field-effect transistor, an organic laser, and a downward conversion device.
[0497] In a preferred embodiment, the optoelectronic device is a device selected from the group consisting of an organic light emitting diode (OLED), a light emitting electrochemical cell (LEC), and a light emitting transistor.
[0498] In one embodiment of the inventive optoelectronic device, the inventive organic molecule E is used as emissive material in the emissive layer EML.
[0499] In one embodiment of the optoelectronic device of the present invention, the light-emitting layer EML consists of the composition according to the present invention described herein.
[0500] When the optoelectronic device is an OLED, it can have, for example, the following layer structure: 1. Substrate 2. Anode layer A 3. Hole injection layer (HIL) 4. Hole transport layer (HTL) 5. Electron Blocking Layer (EBL) 6. Emitting layer (EML) 7. Hole-Blocking Layer (HBL) 8.Electron transport layer (ETL) 9.Electron injection layer (EIL) 10. Cathode layer
[0501] Here, the OLED selectively includes each layer selected from the group of HIL, HTL, EBL, HBL, ETL, and EIL, and different layers are combined, and the OLED may also include one or more layers of each layer type defined above.
[0502] In one embodiment, the optoelectronic device also includes one or more protective layers that protect the device from harmful exposure to harmful species, for example, in environments containing moisture, vapors, and / or gases.
[0503] In one embodiment of the present invention, the optoelectronic device is an OLED having the following inverted layer structure: 1. Substrate 2. Cathode layer 3.Electron injection layer (EIL) 4.Electron transport layer (ETL) 5. Hole-Blocking Layer (HBL) 6. Emitting layer B 7. Electron Blocking Layer (EBL) 8. Hole transport layer (HTL) 9. Hole injection layer (HIL) 10. Anode layer A
[0504] Here, the OLED may include only selective layers selected from the group consisting of HIL, HTL, EBL, HBL, ETL, and EIL, and different layers may be combined, and the OLED may include one or more layers of each layer type defined above.
[0505] In one embodiment of the present invention, the optoelectronic device is an OLED that can have a stacked structure. In this structure, each unit is stacked on top of the other, unlike the typical arrangement in which the OLEDs are arranged side by side. Mixed light is generated by the OLED that exhibits the stacked structure. Specifically, white light can be generated by stacking blue, green, and red OLEDs. The OLED that exhibits the stacked structure also includes a charge generation layer (CGL), which is generally located between two OLED subunits and generally consists of an n-doped layer and a p-doped layer, with the n-doped layer of one CGL layer being closer to the anode layer.
[0506] In one embodiment of the present invention, the optoelectronic device is an OLED comprising two or more light-emitting layers between an anode and a cathode. Specifically, the so-called tandem OLED comprises three light-emitting layers, where one light-emitting layer emits red light, one light-emitting layer emits green light, and one light-emitting layer emits blue light, and optionally further comprises a charge-generating layer, a blocking layer, or a transport layer between each light-emitting layer. In another embodiment, the light-emitting layers are stacked adjacent to each other. In another embodiment, the tandem OLED comprises a charge-generating layer between each two light-emitting layers. Also, adjacent light-emitting layers or light-emitting layers separated by a charge-generating layer may be fused together.
[0507] The substrate can be made of any material or material composition. In most cases, a glass slide is used as the substrate. Alternatively, a thin metal layer (e.g., a copper, gold, silver, or aluminum film), a plastic film, or a slide can be used. This allows the substrate to have even greater flexibility. The anode layer A is made of a material that can obtain a nearly (substantially) transparent film. To allow light emission from the OLED, at least one of the two electrodes must be (substantially) transparent, so either the anode layer A or the cathode layer C is transparent. Preferably, the anode layer A contains a high content of transparent conductive oxide (TCO) or even consists of TCO. Such anode layers A may include, for example, indium tin oxide, aluminum zinc oxide, fluorine-doped tin oxide, indium zinc oxide, PbO, SnO, zirconium oxide, molybdenum oxide, vanadium oxide, tungsten oxide, graphite, doped Si, doped Ge, doped GaAs, doped polyaniline, doped polypyrrole, and / or doped polythiophene.
[0508] The anode layer A is (essentially) indium tin oxide (ITO) (e.g., (InO3) 0.9 (SnO2) 0.1 The roughness of the anode layer A, which is made of a transparent conductive oxide (TCO), can be complemented by the use of a hole injection layer (HIL). The HIL also facilitates the injection of quasi-charge carriers (i.e., holes) in that it facilitates quasi-charge carrier transport from the TCO to the hole transport layer (HTL). The hole injection layer (HIL) may comprise poly-3,4-ethylenedioxythiophene (PEDOT), polystyrene sulfonate (PSS), MoO2, VO5, CuPC, or CuI, specifically a mixture of PEDOT and PSS. The HIL may also prevent metal diffusion from the anode layer A to the hole transport layer (HTL). Examples of HILs include PEDOT:poly-3,4-ethylenedioxythiophene:polystyrene sulfonate (PSS), poly-3,4-ethylenedioxythiophene (PEDOT), 4,4',4"-tris[phenyl(m-tolyl)amino]triphenylamine (mMTDATA), 2,2',7,7'-tetrakis(n,n-diphenylamino)-9,9'-spirobifluorene (spiro-TAD), N1,N1'-(biphenyl-4,4'-diphenyl)- ... )bis(N1-phenyl-N4,N4-di-m-tolylbenzene-1,4-diamine (DNTPD), N,N'-bis-(1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine (NPB), N,N'-diphenyl-N,N'-di-[4-(N,N-diphenyl-amino)phenyl]benzidine (NPNPB), N,N,N',N'-tetrakis(4-methoxyphenyl)benzidine (MeO-TPD), 1, 2,3,6,7,10,11-Hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CN) and / or N,N'-diphenyl-N,N'-bis-(1-naphthyl)-9,9'-spirobifluorene-2,7-diamine (spiro-NPD).
[0509] Generally, the hole transport layer (HTL) is located adjacent to the anode layer A or the hole injection layer (HIL). Any hole transport compound can be used here. For example, electron-rich heteroaromatic compounds such as triarylamines and / or carbazoles can be used as hole transport compounds. The HTL can reduce the energy barrier between the anode layer A and the light-emitting layer (EML). The hole transport layer (HTL) also serves as an electron blocking layer (EBL). Preferably, the hole transport compound has a triplet state T1 with a relatively high energy level. For example, the hole transport layer (HTL) can be tris(4-carbazolyl-9-ylphenyl)amine (TCTA), 2,2'-dimethyl-N,N'-di-[(1-naphthyl)-N,N'-diphenyl]-1,1'-biphenyl-4,4'-diamine (α-NPD), 4,4'-cyclohexylidene-bis[N,N-bis(4-methylphenyl)benzenamine] (TAPC), 4,4',4"-tris[2-naphthyl(phenyl)amino]triphenylamine (2-TNATA), spiro-TAD, DNTPD, NPB, NPNPB, MeO-TPD, HAT-CN and / or star-shaped heterocycles such as 9,9'-diphenyl-6-(9-phenyl-9H-carbazol-3-yl)-9H,9'H-3,3'-bicarbazole (TrisPcz). The HTL may also include a p-doped layer, which may consist of an inorganic or organic dopant in an organic hole-transporting matrix. For example, transition metal oxides such as vanadium oxide, molybdenum oxide, or tungsten oxide may also be used as inorganic dopants. For example, tetrafluorotetracyanoquinodimethane (F4-TCNQ), copper-pentafluorobenzoate (Cu(I)pFBz), or transition metal complexes may also be used as organic dopants.
[0510] EBLs may also include, for example, 1,3-bis(carbazol-9-yl)benzene (mCP), TCTA, 2-TNATA, 3,3-di(9H-carbazol-9-yl)biphenyl (mCBP), tris-Pcz, 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CzSi), and / or N,N'-dicarbazolyl-1,4-dimethylbenzene (DCB).
[0511] Generally, the emissive layer (EML) is located adjacent to the hole-transporting layer (HTL). The emissive layer (EML) comprises at least one emissive molecule. Specifically, the EML comprises at least one emissive molecule E according to the present invention. In one embodiment, the emissive layer comprises only organic molecules according to the present invention. Generally, the EML further comprises one or more host materials H. For example, the host material H can be 4,4'-bis-(N-carbazolyl)-biphenyl (CBP), mCP, mCBP, dibenzo[b,d]thiophen-2-yltriphenylsilane (Sif87), CzSi, dibenzo[b,d]thiophen-2-yl)diphenylsilane (Sif88), bis[2-(diphenylphosphino)phenyl]etheroxide (DPEPO), or 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole. 、9 The host material H is generally selected from -[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole, 2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine (T2T), 2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine (T3T), and / or 2,4,6-tris(9,9'-spirobifluoren-2-yl)-1,3,5-triazine (TST). The host material H should generally be selected to exhibit first triplet (T1) and first singlet (S1) energy levels that are energetically higher than those of the organic molecule.
[0512] In one embodiment of the present invention, the EML comprises a so-called mixed host system having at least one hole-dominant host and one electron-dominant host. In a specific example, the EML comprises exactly one light-emitting organic molecule according to the present invention and a mixed host system including T2T as the electron-dominant host and a hole-dominant host selected from CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole, and 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole. In another embodiment, the EML comprises 50 wt % to 80 wt %, preferably 60 wt % to 75 wt %, of a host selected from CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole, and 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole; 10 wt % to 45 wt %, preferably 15 wt % to 30 wt %, of T2T; and 5 wt % to 40 wt %, preferably 10 wt % to 30 wt %, of an emissive molecule according to the present invention.
[0513] An electron transport layer (ETL) may be positioned adjacent to the light-emitting layer (EML). Any electron transporter may be used here. For example, electron-deficient compounds such as benzimidazole, pyridine, triazole, oxadiazole (e.g., 1,3,4-oxadiazole), phosphine oxide, and sulfone may be used. The electron transporter may also be a star-shaped heterocycle such as 1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl (TPBi). The ETL may also include 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), aluminum tris(8-hydroxyquinoline) (Alq), diphenyl-4-triphenylsilylphenyl-phosphine oxide (TSPO), 2,7-di(2,2′-bipyridin-5-yl)triphenyl (BPyTP), dibenzo[b,d]thiophen-2-yltriphenylsilane (Sif87), dibenzo[b,d]thiophen-2-yl)diphenylsilane (Sif88), 1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene (BmPyPhB), and / or 4,4′-bis-[2-(4,6-diphenyl-1,3,5-triazinyl)]-1,1′-biphenyl (BTB). Optionally, the ETL may also be doped with a material such as Liq. The electron transporting layer (ETL) may also block holes, or a hole blocking layer (HBL) may be incorporated.
[0514] Examples of HBL include 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP) (bathocuproine), bis(8-hydroxy-2-methylquinoline)-(4-phenylphenoxy)aluminum (BAlq), 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), aluminum-tris(8-hydroxyquinoline) (Alq), diphenyl-4-triphenylsilylphenyl-phosphine oxide, and the like. oxide (TSPO1), 2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine (T2T), 2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine (T3T), 2,4,6-tris(9,9'-spirobifluoren-2-yl)-1,3,5-triazine (TST), and / or 1,3,5-tris(N-carbazolyl)benzene / 1,3,5-tris(carbazol-9-yl)benzene (TCB / TCP).
[0515] A cathode layer C may be located adjacent to the electron transport layer (ETL). The cathode layer C may, for example, comprise or consist of a metal (e.g., Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, LiF, Ca, Ba, Mg, In, W, or Pd) or a metal alloy. For practical reasons, the cathode layer may also consist of a (substantially) non-transparent metal such as Mg, Ca, or Al. Alternatively, or in addition, the cathode layer C may also comprise graphite and / or carbon nanotubes (CNTs). Alternatively, the cathode layer C may consist of nanoscale silver wires.
[0516] The OLED may optionally further include a protective layer between the electron-transporting layer (ETL) and the cathode layer C (also designated as the electron-injection layer (EIL)), which may include lithium fluoride, cesium fluoride, silver, 8-hydroxyquinolinolatolithium (Liq), Li2O, BaF2, MgO, and / or NaF.
[0517] Optionally, the electron transporting layer (ETL) and / or the hole blocking layer (HBL) also comprise one or more host compounds H.
[0518] To further modify the emission spectrum and / or absorption spectrum of the light-emitting layer (EML), the light-emitting layer (EML) may further include one or more additional emitter molecules F. Such emitter molecules F may be any emitter molecule known in the art. Preferably, such emitter molecules F have a structure different from that of molecules E according to the present invention. The emitter molecules F may optionally be TADF emitters. Alternatively, the emitter molecules F may be fluorescent and / or phosphorescent emitter molecules that can selectively modify the emission spectrum and / or absorption spectrum of the light-emitting layer (EML). Exemplarily, triplet and / or singlet excitons may be transferred from the organic emitter molecules according to the present invention to the emitter molecules F before relaxing to the ground state S0, and typically emit light that is red-shifted compared to the light emitted by the organic molecules. Optionally, the emitter molecules F may also induce a two-photon effect (i.e., absorbing two photons at half the maximum absorption energy).
[0519] Optionally, the optoelectronic device (e.g., OLED) may also be essentially a white optoelectronic device. For example, such a white optoelectronic device may include at least one blue (deep blue) emitter molecule and one or more emitter molecules that emit green and / or red light. Also, as mentioned above, there may be optional energy transmission between two or more molecules.
[0520] As used herein, unless more specifically defined in a particular context, the hue designations of emitted and / or absorbed light are as follows: Purple: wavelength range of >380nm to 420nm Deep blue: wavelength range of >420nm to 480nm Sky blue color: wavelength range of >480nm~500nm Green: wavelength range of >500nm to 560nm Yellow: wavelength range of >560nm to 580nm Orange: wavelength range of >580nm to 620nm Red: wavelength range of >620nm to 800nm Associated with the emitter molecule, such hues exhibit emission maxima. Thus, for example, a deep blue emitter has an emission maximum in the range >420 nm to 480 nm, a sky blue emitter has an emission maximum in the range >480 nm to 500 nm, a green emitter has an emission maximum in the range >500 nm to 560 nm, and a red emitter has an emission maximum in the range >620 nm to 800 nm.
[0521] Deep blue emitters can preferably have an emission maximum below 480 nm, preferably below 470 nm, even more preferably below 465 nm, or more preferably below 460 nm, and are generally exhibited with an emission maximum above 420 nm, preferably above 430 nm, even more preferably above 440 nm, or more preferably above 450 nm.
[0522] Green emitters have an emission maximum below 560 nm, preferably below 550 nm, even more preferably below 545 nm, or even more preferably below 540 nm, and are generally given an emission maximum above 500 nm, preferably above 510 nm, even more preferably above 515 nm, or even more preferably above 520 nm.
[0523] Therefore, in yet another aspect of the present invention, 2 and / or has an external quantum efficiency of greater than 8%, preferably greater than 10%, more preferably greater than 13%, even more preferably greater than 15%, or more preferably greater than 20%, and / or has an emission maximum of 420 nm to 500 nm, preferably 430 nm to 490 nm, even more preferably 440 nm to 480 nm, even more preferably 450 nm to 470 nm, and / or has an emission maximum of 500 cd / m 2In particular, the present invention relates to an OLED having an LT80 value of greater than 100 hours, preferably greater than 200 hours, more preferably greater than 400 hours, even more preferably greater than 750 hours, or more preferably greater than 1,000 hours. Accordingly, yet another aspect of the present invention relates to an OLED having an emission exhibiting a CIEy color coordinate of less than 0.45, preferably less than 0.30, more preferably less than 0.20, or even more preferably less than 0.15, or more preferably less than 0.10.
[0524] Yet another aspect of the present invention relates to OLEDs that emit light at distinct color points. According to the present invention, the OLEDs emit light with a narrow emission band (small full width at half maximum (FWHM)). In one aspect, OLEDs according to the present invention emit light with a main emission peak FWHM of less than 0.25 eV, preferably less than 0.20 eV, more preferably less than 0.17 eV, even more preferably less than 0.15 eV, or more preferably less than 0.13 eV.
[0525] Yet another aspect of the present invention relates to an OLED that emits light having color coordinates CIEx and CIEy close to the color coordinates CIEx (=0.131) and CIEy (=0.046) of primary blue (CIEx=0.131 and CIEy=0.046) defined in ITU-R Recommendation BT.2020 (Rec.2020), which is suitable for use in ultra-high definition (UHD) displays such as UHD-TVs. Thus, yet another aspect of the present invention relates to an OLED whose emission exhibits a CIEx color coordinate of 0.02 to 0.30, preferably 0.03 to 0.25, more preferably 0.05 to 0.20, even more preferably 0.08 to 0.18, or more preferably 0.10 to 0.15, and / or a CIEy color coordinate of 0.00 to 0.45, preferably 0.01 to 0.30, more preferably 0.02 to 0.20, even more preferably 0.03 to 0.15, or more preferably 0.04 to 0.10.
[0526] Some embodiments of the present invention relate to OLEDs that emit light with color coordinates CIEx (=0.170) and CIEy (=0.797) close to the color coordinates of primary green (CIEx=0.170 and CIEy=0.797) defined in ITU-R Recommendation BT.2020 (Rec.2020), making them suitable for use in ultra-high definition (UHD) displays such as UHD-TVs. In the above context, the term "close" refers to the range of CIEx and CIEy coordinates provided at the end of this paragraph. While top-emitting devices (where the top electrode is transparent) are commonly used in commercial applications, the test devices used throughout the present invention are bottom-emitting devices (where the bottom electrode and substrate are transparent). Accordingly, another aspect of the present invention relates to an OLED whose emission exhibits a CIEx color coordinate of 0.15 to 0.45, preferably 0.15 to 0.35, more preferably 0.15 to 0.30, even more preferably 0.15 to 0.25, or more preferably 0.15 to 0.20, and / or a CIEy color coordinate of 0.60 to 0.92, preferably 0.65 to 0.90, more preferably 0.70 to 0.88, even more preferably 0.75 to 0.86, or more preferably 0.79 to 0.84.
[0527] Therefore, in yet another aspect of the present invention, 2 and / or an external quantum efficiency of greater than 8%, preferably greater than 10%, more preferably greater than 13%, even more preferably greater than 15% or greater than 17%, more preferably greater than 20%, and / or an emission maximum between 485 nm and 560 nm, preferably between 500 nm and 560 nm, even more preferably between 510 nm and 550 nm, even more preferably between 515 nm and 540 nm, and / or a maximum emission of 14,500 cd / m 2 The present invention relates to an OLED having an LT97 value of more than 100 hours, preferably more than 250 hours, more preferably more than 500 hours, even more preferably more than 750 hours, or even more preferably more than 1,000 hours.
[0528] In yet another embodiment of the present invention, the composition has a photoluminescence quantum yield (PLQY) at ambient temperature of greater than 20%, preferably greater than 30%, more preferably greater than 35%, even more preferably greater than 40%, even more preferably greater than 45%, even more preferably greater than 50%, even more preferably greater than 55%, even more preferably greater than 60%, or more preferably greater than 70%.
[0529] In yet another aspect, the present invention relates to a method for manufacturing an optoelectronic device, in which the organic molecules of the present invention are used.
[0530] The optoelectronic device, in particular the OLED according to the present invention, can be fabricated by any vapor deposition and / or liquid processing method. - Prepared through the sublimation process - Manufactured by organic vapor phase deposition process, - produced by a carrier gas sublimation process, or - Solution processed or printed.
[0531] The methods used to fabricate optoelectronic devices, particularly OLEDs according to the present invention, are known in the art. The different layers are deposited individually and successively on a suitable substrate by subsequent deposition steps. The individual layers may be deposited using the same or different deposition methods.
[0532] For example, vapor deposition processes include thermal (co)evaporation, chemical vapor deposition, and physical vapor deposition. In the case of an active matrix OLED display, an AMOLED backplane is used as the substrate. Individual layers can be processed by solution or dispersion using appropriate solvents. For example, solution deposition processes include spin coating, dip coating, and jet printing. Liquid processing can optionally be performed in an inert atmosphere (e.g., nitrogen atmosphere), and the solvent can be completely or partially removed by means known in the art. [Example]
[0533] General synthesis method I [ka]
[0534] General synthesis method II [ka]
[0535] General procedure for synthesis: AAV1: I0 (1.00 equiv.), 3,5-dichloro-iodobenzene (I0-1, 0.8 equiv.), palladium(II) acetate (0.03 equiv.), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (S-Phos, CAS: 657408-07-6, 0.06 equiv.), and potassium phosphate tribasic (K3PO4, 3.00 equiv.) are stirred in a dioxane / water mixture under a nitrogen atmosphere at 90 °C for 12 h. After cooling to room temperature (rt), the reaction mixture is extracted with DCM and brine. After phase separation, the solvent is removed under reduced pressure. The crude material is purified by column chromatography to give I-1 in 84% yield. GC-MS: 313.02 m / z.
[0536] AAV2: I-1 (1.00 equiv.), diphenylamine (CAS: 122-39-4, 2.5 equiv.), tris(dibenzylideneacetone)dipalladium(0) (CAS: 51364-51-3, 0.01 equiv.), tri-tert-butylphosphine (CAS: 13716-12-6, 0.04 equiv.), and sodium tert-butoxide (CAS: 865-48-5, 4.00 equiv.) were stirred in dry toluene under a nitrogen atmosphere at 100 °C for 12 h. After cooling to room temperature (rt), the reaction mixture was washed with water and brine. After phase separation, the solvent was removed under reduced pressure. The resulting material was purified by recrystallization to give I-2 in 45% yield. LC-MS: 578.40 m / z (4.69 min at rt).
[0537] AAV3: I-2 (1.00 eq.) is placed in a round-bottom flask under nitrogen. Solvent (1,2-dichlorobenzene) is added. Boron tribromide (CAS: 10294-33-4, 6.00 eq.) is added dropwise and heated to 180°C. After cooling to room temperature, further cooling is performed to 0°C. DIPEA (CAS: 7087-68-5, 10.00 eq.) is added and stirred for 1 hour. The reaction mixture is washed with water, and after phase separation, the solvent is removed under reduced pressure. The resulting material is purified by column chromatography to give P in 32% yield. LC-MS: 586 m / z (5.73 min at room temperature).
[0538] General synthesis method III [ka]
[0539] General procedure for synthesis: AAV4: E1 (1.00 equiv.), bis(pinacolato)diboron (CAS: 73183-34-3, 1.0 equiv.), tris(dibenzylideneacetone)dipalladium (CAS: 51364-51-3, 0.02 equiv.), 2-dicyclohexylphosphino-2',4',6'-tri-isopropyl-1,1'-biphenyl (X-Phos, CAS: 564483-18-7, 0.08 equiv.), and potassium acetate (KOAc, CAS: 127-08-2, 2.00 equiv.) were stirred in dry toluene under a nitrogen atmosphere at 105 °C for 24 h. After cooling to room temperature (rt), the reaction mixture was extracted with ethyl acetate and brine, and the combined organic layers were concentrated under reduced pressure. The resulting material was purified via column chromatography or recrystallization to give I-4 as a solid.
[0540] AAV5: I-4 (1.00 equiv.), E2 (1.0 equiv.), tris(dibenzylideneacetone)dipalladium(0) (CAS: 51364-51-3, 0.01 equiv.), S-Phos (CAS: 657408-07-6, 0.04 equiv.), and potassium phosphate tribasic (KPO, CAS: 7778-53-2, 3.00 equiv.) are stirred in a dioxane / water mixture under a nitrogen atmosphere at 100 °C for 2 h. The reaction mixture is cooled to room temperature (rt) and then washed with water and brine. The combined organic layers are dried over MgSO, filtered, and concentrated under reduced pressure. The resulting material is recrystallized or purified by column chromatography to give I-5 as a solid.
[0541] AAV6: I-5 (1.00 eq.) is placed in a round-bottom flask under nitrogen. A solvent (1,2-dichlorobenzene) is added. Boron tribromide (CAS: 10294-33-4, 4.00 eq.) is added dropwise and heated to 180°C overnight. After cooling to room temperature, the mixture is further cooled to 0°C. DIPEA (CAS: 7087-68-5, 10.00 eq.) is added and stirred for 1 hour. The reaction mixture is washed with water, and after phase separation, the solvent is removed under reduced pressure. The resulting material is purified via column chromatography or recrystallization to give P-1 as a solid.
[0542] General synthesis method IV [ka]
[0543] General procedure for synthesis: AAV7: E3 (2.00 equiv.), E4 (1.0 equiv.), tris(dibenzylideneacetone)dipalladium(0) (CAS: 51364-51-3, 0.01 equiv.), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (S-Phos, CAS: 657408-07-6, 0.04 equiv.), and potassium phosphate tribasic (KPO, 3.00 equiv.) are stirred in a THF / water mixture under a nitrogen atmosphere at 80 °C. After cooling to room temperature (rt), the reaction mixture is extracted with ethyl acetate and brine. After phase separation, the solvent is removed under reduced pressure. The resulting material is purified via column chromatography or recrystallization to give I-6 as a solid.
[0544] AAV8: I-6 (1.00 equiv.), E5 (1.00 equiv.), tris(dibenzylideneacetone)dipalladium(0) (CAS: 51364-51-3, 0.01 equiv.), tri-tert-butylphosphine (CAS: 13716-12-6, 0.04 equiv.), and sodium tert-butoxide (CAS: 865-48-5, 3.00 equiv.) are stirred in dry toluene under a nitrogen atmosphere at 110 °C for 72 h. After cooling to room temperature (rt), the reaction mixture is washed with water and brine. The phases are separated and the solvent is removed under reduced pressure. The resulting material is recrystallized or purified by column chromatography to give I-7 as a solid.
[0545] AAV9: I-7 (1.00 eq.) is placed in a round-bottom flask under nitrogen. A solvent (1,2-dichlorobenzene) is added. Boron tribromide (CAS: 10294-33-4, 4.00 eq.) is added dropwise and heated to 180°C. After cooling to room temperature, the mixture is further cooled to 0°C. DIPEA (CAS: 7087-68-5, 10.00 eq.) is added and stirred for 1 hour. The reaction mixture is washed with water, and the phases are separated, followed by removal of the solvent under reduced pressure. The resulting material is purified via column chromatography or recrystallization to give P-2 as a solid.
[0546] General synthesis method V [ka]
[0547] General procedure for synthesis: AAV10: E5 (1.05 equiv.), E6 (1.00 equiv.), tris(dibenzylideneacetone)dipalladium(0) (CAS: 51364-51-3, 0.005 equiv.), sodium tert-butoxide (NaOtBu, CAS: 865-48-5, 1.50 equiv.), and tri-tert-butylphosphonium tetrafluoroborate (P(tBu)HBF, CAS: 131274-22-1, 0.02 equiv.) are stirred overnight in dry toluene at 100 °C under a nitrogen atmosphere. After cooling the reaction mixture to room temperature (rt), water is added, and the phases are separated. The combined organic layer is dried over MgSO, filtered, and concentrated under reduced pressure. The resulting material is purified via column chromatography or recrystallization to give I-8 as a solid.
[0548] AAV11: I-8 (1.00 equiv.), E3 (1.2 equiv.), tris(dibenzylideneacetone)dipalladium(0) (CAS: 51364-51-3, 0.01 equiv.), X-Phos (CAS: 564483-18-7, 0.04 equiv.), and potassium phosphate tribasic (KPO, CAS: 7778-53-2, 2.00 equiv.) are stirred in a THF / water mixture under a nitrogen atmosphere at 80 °C for 96 h. After cooling to room temperature (rt), the reaction mixture is washed with water and brine, and the combined organic layers are dried over MgSO, filtered, and concentrated under reduced pressure. The resulting material is recrystallized or purified by column chromatography to give I-7 as a solid.
[0549] The final reaction step is carried out as described for AAV9, where: 1,2-di Chlorobenzene was used as the solvent and the reaction temperature was 180 It was °C.
[0550] General synthesis method VI [ka]
[0551] General procedure for synthesis: The initial reaction steps were carried out as described for AAV7. AAV12: I-6 (2.00 equiv.), E7 (1.0 equiv.), tris(dibenzylideneacetone)dipalladium(0) (CAS: 51364-51-3, 0.01 equiv.), tri-tert-butylphosphine (CAS: 13716-12-6, 0.04 equiv.), and sodium tert-butoxide (CAS: 865-48-5, 6.00 equiv.) were stirred in dry toluene under a nitrogen atmosphere at 110 °C for 72 h. After cooling to room temperature (rt), the reaction mixture was extracted with ethyl acetate and brine. After phase separation, the solvent was removed under reduced pressure. The resulting material was recrystallized or purified by column chromatography to give I-9 as a solid.
[0552] AAV13: I-9 (1.00 equivalents) is placed in a round-bottom flask under nitrogen. The solvent 1,2-dichlorobenzene is added. Boron tribromide (CAS: 10294-33-4, 6.00 equivalents) is added dropwise and heated to 180°C. After cooling to room temperature, the mixture is further cooled to 0°C. DIPEA (CAS: 7087-68-5, 10.00 equivalents) is added and stirred for 1 hour. The reaction mixture is washed with water, and the phases are separated, followed by removal of the solvent under reduced pressure. The resulting material is purified via column chromatography or recrystallization to give P-3 as a solid.
[0553] General synthesis method VII [ka]
[0554] General procedure for synthesis: AAV14: E5 (2.10 equiv.), E8 (1.00 equiv.), tris(dibenzylideneacetone)-dipalladium(0) (CAS: 51364-51-3, 0.01 equiv.), sodium tert-butoxide (NaOtBu, CAS: 865-48-5, 3.15 equiv.), and tri-tert-butylphosphine (P(tBu)3, CAS: 13716-12-6, 0.04 equiv.) are stirred in dry toluene under a nitrogen atmosphere at 110 °C for 1 h. After cooling to room temperature (rt), the reaction mixture is extracted with ethyl acetate and brine, and the combined organic layers are concentrated under reduced pressure. The resulting material is purified via column chromatography or recrystallization to give I-10 as a solid.
[0555] AAV15: I-10 (1.00 equiv.), E3 (1.2 equiv.), palladium(II) acetate (CAS: 3375-31-3, 0.06 equiv.), X-Phos (CAS: 564483-18-7, 0.12 equiv.), and potassium phosphate tribasic (KPO, CAS: 7778-53-2, 3.00 equiv.) are stirred in a dioxane / water mixture under a nitrogen atmosphere at 100 °C for 55 h. After cooling to room temperature (rt), the reaction mixture is extracted with toluene and brine, and the combined organic layers are concentrated under reduced pressure. The resulting material is recrystallized or purified by column chromatography to give I-11 as a solid.
[0556] AAV0-3: Under nitrogen, I-11 (1.00 equivalents) is dissolved in tert-butylbenzene. At 20°C, n-BuLi (2.5 M in hexane, CAS: 109-72-8, 1.1 equivalents) is added and the mixture is stirred for 15 minutes. Next, t-BuLi (1 M in pentane, CAS: 594-19-4, 2.2 equivalents) is added and the mixture is stirred at 60°C for 2 hours. Then, the mixture is - 78After cooling to below 20°C, BBr3 (CAS: 10294-33-4, 1.3 equivalents) is added dropwise. The mixture is allowed to warm to room temperature and then stirred at room temperature for 16 hours. The mixture is extracted with ethyl acetate and water, and the combined organic layers are concentrated under reduced pressure. The resulting material is purified by column chromatography or recrystallization to give the target compound as a solid.
[0557] General synthesis method VIII [ka]
[0558] General procedure for synthesis: AAV16: E3 (1.00 equiv.), E9 (1.1 equiv.), tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4, CAS: 14221-01-3, 0.02 equiv.), and potassium carbonate (K2CO3, 2.00 equiv.) are stirred in a THF / water mixture under a nitrogen atmosphere at 80 °C for 48 h. After cooling to room temperature (rt), the phases are separated and the aqueous layer is extracted with ethyl acetate. The combined organic layers are dried over MgSO4, filtered, and concentrated under reduced pressure. The resulting material is purified via column chromatography or recrystallization to give I-12 as a solid.
[0559] AAV17: I-12 (1.00 equiv.), di-tert-butyl dicarbonate (CAS: 24424-99-5, 1.4 equiv.), and 4-dimethylaminopyridine (4-DMAP, CAS: 1122-58-3, 1.00 equiv.) are stirred in dry MeCN under a nitrogen atmosphere at room temperature for 16 hours. NaOH solution (1 M) is added to the reaction mixture, and the phases are separated. The aqueous layer is extracted with ethyl acetate. The combined organic layers are washed with water and brine, then dried over MgSO4, filtered, and concentrated under reduced pressure. The resulting material is purified via column chromatography or recrystallization to give I-13 as a solid.
[0560] AAV18: I-13 (1.00 equiv.), E5 (1.20 equiv.), tris(dibenzylideneacetone)dipalladium(0) (CAS: 51364-51-3, 0.01 equiv.), tri-tert-butylphosphonium tetrafluoroborate (CAS: 131274-22-1, 0.04 equiv.), and sodium tert-butoxide (CAS: 865-48-5, 2.00 equiv.) are stirred in dry toluene under a nitrogen atmosphere at 110 °C for 16 h. After cooling to room temperature (rt), the reaction mixture is washed with water, and the aqueous layer is extracted with ethyl acetate. The combined organic layers are dried over MgSO, filtered, and concentrated under reduced pressure. The resulting material is recrystallized or purified by column chromatography to give I-14 as a solid.
[0561] AAV19: I-14 (1.00 equiv.) is dissolved in dichloromethane (DCM). Trifluoroacetic acid (CAS: 76-05-1; 99.7 equiv.) is added at room temperature, and the reaction mixture is stirred for 2 hours. The phases are then separated, and the TFA layer is extracted with DCM. The combined organic layers are washed with saturated NaHCO3 solution and water, then dried over MgSO4, and filtered. After removing the solvent under reduced pressure, the resulting material is recrystallized or purified by column chromatography to give I-15 as a solid.
[0562] AAV20: I-15 (1.00 eq.) is placed in a round-bottom flask under nitrogen. The solvent o-xylene is added. At 0°C, n-butyllithium (2.5 M in hexane, CAS: 109-72-8, 1.10 eq.) is added dropwise and the mixture is stirred for 15 minutes. Then, tert-butyllithium (1.6 M in hexane, CAS: 594-19-4, 2.20 eq.) is added dropwise and the temperature is increased to 6°C. 0 The temperature is increased to °C and the reaction mixture is stirred for 2 hours. The reaction mixture is cooled to room temperature. 0At 0°C, boron tribromide (1M in heptane, CAS: 10294-33-4, 1.30 equivalents) is added dropwise, and the mixture is stirred at 0°C for 1 hour, followed by stirring at room temperature for 6 hours. The reaction mixture is poured into 5% NH3 solution, and the phases are separated, after which the organic layer is washed with water. The organic layer is dried over MgSO4, filtered, and concentrated under reduced pressure. The resulting material is purified via column chromatography or recrystallization to give P-5 as a solid.
[0563] General synthesis method IX [ka]
[0564] General procedure for synthesis: AAV21: E10 (1.10 equivalents), E11 (1.00 equivalents), and potassium phosphate tribasic (1.50 equivalents, CAS: 7778-53-2) in dry DMSO are heated at 100°C for 48 hours. The mixture is cooled to room temperature and then poured into ice water. The precipitate is collected by filtration, washed with water and ethanol, and the resulting material is recrystallized or purified by column chromatography to give compound I-16 as a solid.
[0565] AAV22: Under nitrogen, I-16 (1.00 equivalents) was reacted with E3 (1.00 equivalents), potassium phosphate tribasic (1.80 equivalents, CAS: 7778-53-2), tris(dibenzylideneacetone)dipalladium(0) (0.01 equivalents, CAS: 51364-51-3), and X-Phos (0.04 equivalents, CAS: 564483-18-7) in a toluene / water mixture (8:1 volume ratio) at 95 °C for 48 hours. After cooling to room temperature, the phases were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The resulting material was purified by column chromatography or recrystallization to give compound I-17 as a solid.
[0566] AAV23: Under nitrogen, I-17 (1.00 equivalents) was reacted with E12 (1.50 equivalents), potassium phosphate tribasic (3.00 equivalents, CAS: 7778-53-2), tris(dibenzylideneacetone)dipalladium(0) (0.01 equivalents, CAS: 51364-51-3), and X-Phos (0.04 equivalents, CAS: 564483-18-7) in a dioxane / water mixture (5:1 volume ratio) at 100°C for 5 hours. After cooling to room temperature, the phases were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The resulting material was purified by column chromatography or recrystallization to give compound I-18 as a solid.
[0567] The final reaction step is AAV 20 was carried out as described in.
[0568] General synthesis method [ka]
[0569] General procedure for synthesis: AAV24: E13 (1.10 equivalents), E11 (1.00 equivalents), and potassium phosphate tribasic (1.50 equivalents, CAS: 7778-53-2) in dry DMSO are heated at 100°C for 48 hours. The mixture is cooled to room temperature and then poured into ice water. The precipitate is collected by filtration, washed with water and ethanol, and the resulting material is recrystallized or purified by column chromatography to give compound I-19 as a solid.
[0570] AAV25: Under nitrogen, I-19 (1.00 equivalents) was reacted with E3 (1.20 equivalents), potassium phosphate tribasic (2.00 equivalents, CAS: 7778-53-2), tris(dibenzylideneacetone)dipalladium(0) (0.01 equivalents, CAS: 51364-51-3), and X-Phos (0.04 equivalents, CAS: 564483-18-7) in a toluene / water mixture (8:1 volume ratio) at 100°C for 5 hours. After cooling to room temperature, the phases were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The resulting material was purified by column chromatography or recrystallization to give compound I-20 as a solid.
[0571] The final reaction step is AAV 20 was carried out as described in.
[0572] General synthesis method XI [ka]
[0573] General procedure for synthesis: AAV26: Under nitrogen, E14 (1.00 equivalents) is reacted with E3 (1.00 equivalents), potassium carbonate (2.00 equivalents, CAS: 584-08-7), tris(dibenzylideneacetone)dipalladium(0) (0.02 equivalents, CAS: 51364-51-3), and S-Phos (0.08 equivalents, CAS: 657408-07-6) in a dioxane / water mixture (10:1 volume ratio) at 90 °C for 72 hours. After cooling to room temperature, the phases are separated and the aqueous layer is extracted with ethyl acetate. The combined organic layers are dried over MgSO4, filtered, and concentrated under reduced pressure. The resulting material is purified by column chromatography or recrystallization to give compound I-21 as a solid.
[0574] AAV27: E5 (1.00 equiv.), E14 (1.00 equiv.), tris(dibenzylideneacetone)-dipalladium(0) (CAS: 51364-51-3, 0.01 equiv.), sodium tert-butoxide (NaOtBu, CAS: 865-48-5, 3.00 equiv.), and tri-tert-butylphosphine (P(tBu)3, CAS: 13716-12-6, 0.04 equiv.) are stirred in dry toluene under a nitrogen atmosphere at 110 °C for 24 h. After cooling to room temperature (rt), the reaction mixture is extracted with ethyl acetate and brine, and the combined organic layers are concentrated under reduced pressure. The resulting material is purified via column chromatography or recrystallization to give I-22 as a solid.
[0575] AAV28: In dry dichlorobenzene under nitrogen, I-22 (1.00 equivalents) is reacted with BBr3 (3.00 equivalents, CAS: 10294-33-4) at 135°C for 45 minutes. After the mixture is cooled to room temperature, it is further cooled to 0°C, and then DIPEA (10.0 equivalents, CAS: 7087-68-5) is added. After adding water, the phases are separated, and the aqueous layer is extracted with dichloromethane. The combined organic layer is washed with water, then dried over MgSO4, filtered, and concentrated. The resulting material is purified by column chromatography or recrystallization to obtain compound P-8 as a solid.
[0576] General synthesis method XII [ka]
[0577] General procedure for synthesis: AAV29: E5 (1.05 equiv.), E14 (1.00 equiv.), tris(dibenzylideneacetone)-dipalladium(0) (CAS: 51364-51-3, 0.005 equiv.), sodium tert-butoxide (NaOtBu, CAS: 865-48-5, 1.50 equiv.), and tri-tert-butylphosphonium tetrafluoroborate (HP(tBu)3BF4, CAS: 131274-22-1, 0.02 equiv.) are stirred in dry toluene under a nitrogen atmosphere at 100°C for 1 hour. After cooling to room temperature (rt), the reaction mixture is extracted with ethyl acetate and brine, and the combined organic layers are concentrated under reduced pressure. The resulting material is purified via column chromatography or recrystallization to give I-23 as a solid.
[0578] AAV30: Under nitrogen, I-23 (1.00 equivalents) was reacted with E3 (1.10 equivalents), potassium phosphate tribasic (2.00 equivalents, CAS: 7778-53-2), tris(dibenzylideneacetone)dipalladium(0) (0.01 equivalents, CAS: 51364-51-3), and S-Phos (0.04 equivalents, CAS: 657408-07-6) in a dioxane / water mixture (5:1 volume ratio) at 100°C for 48 hours. After cooling to room temperature, the phases were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The resulting material was purified by column chromatography or recrystallization to give compound I-24 as a solid.
[0579] AAV31: In dry dichlorobenzene under nitrogen, I-24 (1.00 equivalents) is reacted with BBr3 (3.00 equivalents, CAS: 10294-33-4) at 90°C for 1 hour. After the mixture is cooled to room temperature, it is further cooled to 0°C, and then DIPEA (10.0 equivalents, CAS: 7087-68-5) is added. After adding water, the phases are separated, and the aqueous layer is extracted with dichloromethane. The combined organic layer is washed with water, then dried over MgSO4, filtered, and concentrated. The resulting material is purified by column chromatography or recrystallization to obtain compound P-9 as a solid.
[0580] General synthesis method XIII [ka]
[0581] General procedure for synthesis: AAV32: Under nitrogen, E3 (1.00 equivalents) is reacted with E9 (1.30 equivalents), potassium carbonate (2.00 equivalents, CAS: 584-08-7), and tetrakis(triphenylphosphine)palladium(0) (0.03 equivalents, CAS: 14221-01-3) in a dioxane / water mixture (4:1 volume ratio) at 80°C for 8 hours. After cooling to room temperature, the phases are separated and the aqueous layer is extracted with ethyl acetate. The combined organic layers are dried over MgSO4, filtered, and concentrated under reduced pressure. The resulting material is purified by column chromatography or recrystallization to give compound I-12 as a solid.
[0582] AAV33:E5 (1.10 equiv.), I-12 (1.00 equiv.), tris(dibenzylideneacetone)-dipalladium(0) (CAS: 51364-51-3, 0.01 equiv.), sodium tert-butoxide (NaOtBu, CAS: 865-48-5, 3.20 equiv.), and tri-tert-butylphosphonium tetrafluoroborate (HP(tBu)3BF4, CAS: 131274-22-1, 0.04 equiv.) were stirred in dry toluene under a nitrogen atmosphere at 110 °C for 3 h. After cooling to room temperature (rt), the reaction mixture was extracted with ethyl acetate and brine, and the combined organic layers were concentrated under reduced pressure. The resulting material was purified via column chromatography or recrystallization to give I-15 as a solid.
[0583] AAV34: Dry under nitrogen o-xyleneIn step 3, a solution of I-15 (1.00 equiv.) was added to n-BuLi (2.5 M in hexane, 1.10 equiv., CAS: 109-72-8) at room temperature. After stirring for 15 minutes, t-BuLi (1.6 M in pentane, 2.20 equiv., CAS: 594-19-4) was added, and the mixture was heated at 60° C. for 2 hours. The mixture was then cooled to −60° C., and BBr (1.50 equiv., CAS: 10294-33-4) was added dropwise. The mixture was then stirred at 0° C. for 1 hour and then at room temperature for 16 hours. The mixture was poured into a saturated solution of NaHCO. The phases were separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water, dried over MgSO, filtered, and concentrated. The resulting material was purified by column chromatography or recrystallization to give compound P5 as a solid.
[0584] General synthesis method XIV In the first reaction step, X = N-(C6-C 18 aryl) [ka]
[0585] General procedure for synthesis: AAV35: E15 (1.10 equiv.), E16 (1.00 equiv.), tris(dibenzylideneacetone)-dipalladium(0) (CAS: 51364-51-3, 0.01 equiv.), sodium tert-butoxide (NaOtBu, CAS: 865-48-5, 2.00 equiv.), and tri-tert-butylphosphine (P(tBu)3, CAS: 13716-12-6, 0.04 equiv.) are stirred in dry toluene under a nitrogen atmosphere at 60 °C until the reaction is complete (TLC control). After cooling to room temperature (rt), the reaction mixture is extracted with ethyl acetate and brine, and the combined organic layers are concentrated under reduced pressure. The resulting material is purified via column chromatography or recrystallization to give E-5 as a solid.
[0586] AAV36: E5 (1.00 equiv.), I-21 (1.00 equiv.), tris(dibenzylideneacetone)-dipalladium(0) (CAS: 51364-51-3, 0.01 equiv.), sodium tert-butoxide (NaOtBu, CAS: 865-48-5, 2.00 equiv.), and tri-tert-butylphosphonium tetrafluoroborate (HP(t-Bu)3BF4, CAS: 131274-22-1, 0.02 equiv.) were stirred under reflux in dry toluene under a nitrogen atmosphere until the reaction was complete (TLC control). After cooling to room temperature (rt), the reaction mixture was extracted with toluene and brine, and the combined organic layers were concentrated under reduced pressure. The resulting material was purified via column chromatography or recrystallization to give I-22 as a solid.
[0587] AAV37: I-22 (1.00 eq.) is placed in a round-bottom flask under nitrogen. A solvent (1,2-dichlorobenzene) is added. Boron tribromide (CAS: 10294-33-4, 3.00 eq.) is added dropwise and the reaction is heated to 180°C until completion (TLC control). After cooling to room temperature, the mixture is further cooled to 0°C. DIPEA (CAS: 7087-68-5, 10.00 eq.) is added and the mixture is stirred for 1 hour. The reaction mixture is washed with water, and after phase separation, the solvent is removed under reduced pressure. The resulting material is purified via column chromatography or recrystallization to give P-8 as a solid.
[0588] General synthesis method XV [ka]
[0589] General procedure for synthesis: AAV38: E17 (1.40 equiv.), E18 (0.9 equiv.), and hydroiodic acid (CAS: 10034-85-2, 0.20 equiv.) were stirred in dry acetonitrile under a nitrogen atmosphere at 100°C for 16 hours. After the reaction mixture was cooled to 0°C, the precipitate was filtered and washed with cold acetonitrile. The solid was dissolved in acetonitrile, and iodine (CAS: 7553-56-2, 0.40 equiv.) was added. The mixture was stirred at 100°C until the reaction was complete (TLC monitoring). The reaction mixture was quenched with saturated sodium thiosulfite solution, and the precipitate was washed with cold acetonitrile, methanol, and hexane. The resulting material was recrystallized or purified by column chromatography to give I-25 as a solid.
[0590] AAV39: I-25 (1.00 equiv.), E19 (6.0 equiv.), tris(dibenzylideneacetone)dipalladium(0) (CAS: 51364-51-3, 0.04 equiv.), tri-tert-butylphosphonium tetrafluoroborate (CAS: 131274-22-1, 0.16 equiv.), and sodium tert-butoxide (CAS: 865-48-5, 7.00 equiv.) were stirred in dry toluene under a nitrogen atmosphere at 110 °C for 72 h. After cooling to room temperature (rt), the reaction mixture was extracted with ethyl acetate and brine. After phase separation, the solvent was removed under reduced pressure. The resulting material was recrystallized or purified by column chromatography to give I-26 as a solid.
[0591] AAV40: I-26 (1.00 equiv.) is placed in a round-bottom flask under nitrogen. A solvent (1,2-dichlorobenzene) is added. Boron tribromide (CAS: 10294-33-4, 4.00 equiv.) is added dropwise and the reaction is heated to 180°C until completion (TLC control). After cooling to room temperature, the mixture is further cooled to 0°C. DIPEA (CAS: 7087-68-5, 10.00 equiv.) is added and the mixture is stirred for 1 hour. The reaction mixture is washed with water, and after phase separation, the solvent is removed under reduced pressure. The resulting material is purified via column chromatography or recrystallization to give P-10 as a solid.
[0592] General synthesis method XVI [ka]
[0593] General procedure for synthesis: AAV41: E17 (2.00 equiv.), E20 (1.0 equiv.), and bis(trifluoromethyl)methanol (CAS: 920-66-1, 300 ml) are stirred at room temperature under a nitrogen atmosphere until the reaction is complete (TLC control). After the reaction mixture is cooled to 0°C, the precipitate is filtered and washed with cold acetonitrile. The solid is redissolved in acetonitrile, and 1,4-benzoquinone (CAS: 106-51-4, 0.20 equiv.) is added. The mixture is stirred at room temperature until the reaction is complete (TLC monitoring). The solvent is removed under reduced pressure. The resulting material is recrystallized or purified by column chromatography to give I-27 as a solid. AAV42: I-27 (1.00 equivalents), E21 (1.00 equivalents) are stirred in dichloromethane under nitrogen atmosphere at room temperature. Iodine (CAS: 7553-56-2, 0.03 equivalents) is added, and the mixture is stirred at room temperature until the reaction is complete (TLC monitoring). The solvent is removed under reduced pressure. The resulting material is recrystallized or purified by column chromatography to obtain I-28 as a solid.
[0594] AAV43: I-28 (1.00 equiv.), E19 (2.5 equiv.), tris(dibenzylideneacetone)dipalladium(0) CAS: 51364-51-3, 0.03 equiv.), tri-tert-butylphosphonium tetrafluoroborate (CAS: 131274-22-1, 0.12 equiv.), and sodium tert-butoxide (CAS: 865-48-5, 4.00 equiv.) are stirred in dry toluene under a nitrogen atmosphere at 110 °C until the reaction is complete (TLC control). After cooling to room temperature (rt), the reaction mixture is extracted with ethyl acetate and brine. After phase separation, the solvent is removed under reduced pressure. The resulting material is recrystallized or purified by column chromatography to give I-29 as a solid.
[0595] AAV44: I-29 (1.00 eq.) is placed in a round-bottom flask under nitrogen. The solvent dichlorobenzene is added. Boron tribromide (CAS: 10294-33-4, 4.00 eq.) is added dropwise and the reaction is heated to 70°C until completion (TLC control). After cooling to room temperature, the mixture is further cooled to 0°C. DIPEA (CAS: 7087-68-5, 10.00 eq.) is added and stirred for 1 hour. The reaction mixture is washed with water, and after phase separation, the solvent is removed under reduced pressure. The resulting material is purified via column chromatography or recrystallization to obtain P-11 as a solid.
[0596] E3 generation [ka]
[0597] General procedure for synthesis: AAV45:E22 (1.00 equiv.) is dissolved in dry chloroform, and N-bromoxinimide (CAS: 128-08-5, 1.1 equiv.) is added portionwise at 0°C under a nitrogen atmosphere. The mixture is stirred at room temperature for 4 hours, then extracted with dichloromethane and water, and the combined organic layers are concentrated under reduced pressure. The resulting material is purified via column chromatography or recrystallization to give E2 as a solid. AAV46: E2 (1.00 equiv.), bis(pinacolato)diboron (CAS: 73183-34-3, 1.5 equiv.), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (CAS: 72287-26-4, 0.02 equiv.), and potassium acetate (KOAc, CAS: 127-08-2, 3.00 equiv.) are stirred in dry dioxane under a nitrogen atmosphere at 95 °C for 24 hours. After cooling to room temperature (rt), the reaction mixture is extracted with dichloromethane and water, and the combined organic layer is concentrated under reduced pressure. The resulting material is purified via column chromatography or recrystallization to give E3 as a solid.
[0598] General synthesis method XVII [ka]
[0599] General procedure for synthesis: AAV47: Under nitrogen, E14 (1.00 equivalents) is reacted with bis(pinacolato)diboron (1.50 equivalents, CAS: 73183-34-3), potassium acetate (3.00 equivalents, CAS: 127-08-2), and [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (0.04 equivalents, CAS: 72287-26-4) in a dry dioxane mixture at 100°C for 16 hours. After cooling to room temperature, water is added, the phases are separated, and the aqueous layer is extracted with ethyl acetate. The combined organic layers are dried over MgSO4, filtered, and concentrated under reduced pressure. The resulting material is purified by column chromatography or recrystallization to give compound I-30 as a solid.
[0600] AAV48:E2 (1.00 equiv.), I-30 (1.00 equiv.), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (CAS: 72287-26-4, 0.02 equiv.), and potassium phosphate tribasic (K3O4P, CAS: 7778-53-2, 3.00 equiv.) were stirred in dioxane / water (4:1 volume ratio) under a nitrogen atmosphere at 80 °C for 4 hours. After cooling to room temperature (rt), the reaction mixture was extracted with ethyl acetate and water, and the combined organic layers were concentrated under reduced pressure. The resulting material was purified via column chromatography or recrystallization to give I-21 as a solid.
[0601] The last two reaction steps were carried out as described for AAV27 and AAV28.
[0602] General synthesis method XVIII (In some embodiments, R 1 ≠ H or D) [ka]
[0603] General procedure for synthesis: AAV49: E23 (1.00 equiv.), E24 (1.15 equiv.), tris(dibenzylideneacetone)-dipalladium(0) (CAS: 51364-51-3, 0.01 equiv.), sodium tert-butoxide (NaOtBu, CAS: 865-48-5, 3.20 equiv.), and tri-tert-butylphosphonium tetrafluoroborate (HP(t-Bu)3BF4, CAS: 131274-22-1, 0.04 equiv.) are stirred in dry toluene under a nitrogen atmosphere at 70 °C until the reaction is complete (TLC control). After cooling to room temperature (rt), the reaction mixture is extracted with ethyl acetate and brine, and the combined organic layers are concentrated under reduced pressure. The resulting material is purified via column chromatography or recrystallization to give E5a as a solid.
[0604] AAV50: Under nitrogen, E14 (1.00 equivalents) is reacted with bis(pinacolato)diboron (1.50 equivalents, CAS: 73183-34-3), potassium acetate (3.00 equivalents, CAS: 127-08-2), and [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (0.04 equivalents, CAS: 72287-26-4) in a dry dioxane mixture at 100°C for 16 hours. After cooling to room temperature, water is added, the phases are separated, and the aqueous layer is extracted with ethyl acetate. The combined organic layers are dried over MgSO4, filtered, and concentrated under reduced pressure. The resulting material is purified by column chromatography or recrystallization to give compound I-30 as a solid.
[0605] AAV51:E2 (1.00 equiv.), I-30 (1.00 equiv.), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (CAS: 72287-26-4, 0.02 equiv.), and potassium phosphate tribasic (K3O4P, CAS: 7778-53-2, 3.00 equiv.) were stirred in dioxane / water (4:1 volume ratio) under a nitrogen atmosphere at 80 °C for 4 hours. After cooling to room temperature (rt), the reaction mixture was extracted with ethyl acetate and water, and the combined organic layers were concentrated under reduced pressure. The resulting material was purified via column chromatography or recrystallization to give I-21 as a solid.
[0606] AAV52: E5a (1.10 equiv.), I-21 (1.00 equiv.), tris(dibenzylideneacetone)-dipalladium(0) (CAS: 51364-51-3, 0.02 equiv.), sodium tert-butoxide (NaOtBu, CAS: 865-48-5, 3.20 equiv.), and tri-tert-butylphosphonium tetrafluoroborate (HP(t-Bu)3BF4, CAS: 131274-22-1, 0.08 equiv.) are stirred in dry o-xylol under a nitrogen atmosphere at 120 °C until the reaction is complete (TLC control). After cooling to room temperature (rt), the reaction mixture is extracted with ethyl acetate and brine, and the combined organic layers are concentrated under reduced pressure. The resulting material is purified via column chromatography or recrystallization to give I-31 as a solid.
[0607] AAV53: Under nitrogen, I-31 (1.00 equiv.) is reacted with BBr3 (4.00 equiv., CAS: 10294-33-4) in dry chlorobenzene at -10°C for 3 hours, room temperature for 2 hours, 50°C for 16 hours, and then 70°C for 2 hours. After the mixture is cooled to room temperature, DIPEA (10.0 equiv., CAS: 7087-68-5) is added. After adding water, the phases are separated and the aqueous layer is extracted with ethyl acetate. The combined organic layers are washed with water, dried over MgSO4, filtered, and concentrated. The resulting material is purified by column chromatography or recrystallization to give compound P-12 as a solid.
[0608] cyclic voltmeter Cyclic voltage and current measurements were performed at a concentration of 10 volts in dichloromethane or a suitable solvent and a suitable supporting electrolyte (e.g., 0.1 mol / L tetrabutylammonium hexafluorophosphate). -3 The measurement was carried out at room temperature using a three-electrode assembly (working electrode and counter electrode: Pt wire, reference electrode: Pt wire) in a nitrogen atmosphere, with FeCp2 / FeCp2 as the internal standard. + The HOMO data are corrected against a saturated calomel electrode (SCE) using ferrocene as an internal standard.
[0609] Density functional theory calculations Molecular structures are optimized using the BP86 function and resolution of identity (RI). Excitation energies are calculated using the (BP86) optimized structure using time-dependent DFT (TD-DFT) methods. Orbital and excited-state energies are calculated by the B3LYP function. Def2-SVP basis numbers (and m4-grid for numerical integration) are used. The Turbomole program package is used for all calculations.
[0610] optical physical measurements Sample pretreatment: spin coating Element: Spin150, SPSeuro The sample concentration is 10 mg / ml and is dissolved in a suitable solvent. Program: 1) 3 seconds at 400 U / min, 20 seconds at 1,000 U / min at 1,000 U / min. 3) 10 seconds at 4000 U / min at 1,000 U / min. After coating, the film is dried at 70° C. for 1 minute.
[0611] Photoluminescence spectroscopy and time-correlated single photon coefficient (TCSPC) Normal-state emission spectroscopy is measured on a Horiba Scientific Model FluoroMax-4 equipped with a 150W xenon arc lamp, excitation and emission monochromators, a Hamamatsu R928 photomultiplier tube, and a time-correlated single-photon calculation option. Standard correction methods are used to correct the emission and excitation spectra.
[0612] Excited state lifetimes are determined using the TCSPC method employing the same system, with an FM-2013 instrument and a Horiba Yvon TCSPC hub. Excitation Source: NanoLED370 (wavelength: 371 nm, pulse duration: 1.1 ns) NanoLED290 (wavelength: 294 nm, pulse duration: <1 ns) SpectraLED310 (wavelength: 314nm) SpectraLED355 (wavelength: 355nm) Data analysis (exponential fit) is performed using the DataStation software suite and DAS6 analysis software. The fit is determined using a chi-square test.
[0613] Photoluminescence quantum yield measurements For photoluminescence quantum yield (PLQY) measurements, an Absolute PL quantum yield measurement C9920-03G system (Hamamatsu Photonics) was used. Quantum yields and CIE coordinates were determined using software U6039-05 version 3.6.0.
[0614] The emission maximum is expressed in nm, the quantum yield Φ in %, and the CIE coordinates in x,y values. The PLQY is determined using the following protocol. 1) Quality assurance: Anthracene in ethanol (known concentration) is used as a reference. 2) Excitation wavelength: The absorption maximum of the organic molecule is determined and that wavelength is used to excite the molecule. 3) Measurement
[0615] The quantum yield is measured for a solution or film sample in a nitrogen atmosphere and is calculated using the following formula:
[0616]
number
[0617] where n 光子 indicates the number of photons, and Int indicates the intensity.
[0618] Fabrication and properties of optoelectronic devices Optoelectronic devices such as OLED devices containing the organic molecules according to the present invention can also be fabricated via vacuum deposition. When a layer contains more than one compound, the weight percentage of one or more compounds is expressed as %. The total weight percentage value is 100%, so if no value is specified, the proportion of the compound is the same as the difference between the specified value and 100%.
[0619] Non-fully optimized OLEDs are characterized using standard methods by measuring electroluminescence spectra, and the external quantum efficiency (%) is calculated as a function of intensity using the light sensed by the photodiode and the current. The lifetime of the OLED device is extracted from the change in luminance while operating at a constant current density. The LT50 value corresponds to the time when the measured luminance is reduced to 50% of the initial luminance; similarly, LT80 corresponds to the time when the measured luminance is reduced to 80% of the initial luminance, and LT95 corresponds to the time when the measured luminance is reduced to 95% of the initial luminance.
[0620] Accelerated lifetime measurements are performed (e.g., applying increased current densities, e.g., 500 cd / m 2 In the present invention, the LT80 value is determined using the following formula:
[0621]
number
[0622] Here, L0 denotes the initial luminance at the applied current density.
[0623] The value corresponds to the average of a number of pixels (typically 2-8) and the standard deviation among such pixels is provided.
[0624] HPLC-MS: The HPLC-MS analysis is carried out on an Agilent (1100 series) HPLC equipped with an MS-detector (Thermo LTQXL). An example of a typical HPLC method is as follows: a reversed-phase column 4.6 mm x 150 mm, particle size 3.5 μm from Agilent (ZORBAX Eclipse Plus 95 Å C18, 4.6 x 150 mm, 3.5 μm HPLC column) is used in the HPLC. The HPLC-MS measurement is performed at room temperature (rt) with the following gradient:
[0625] [Table 1]
[0626] [Table 2]
[0627] An injection volume of 5 μL is taken for the measurement from an analyte solution at a concentration of 0.5 mg / mL.
[0628] Probe ionization is performed using an atmospheric pressure chemical ionization (APCI) source in either positive (APCI+) or negative (APCI-) ionization mode.
[0629] Example 1 [ka]
[0630] Example 1 was synthesized by the following process: AAV1 (84% yield) AAV2 (45% yield) AAV3 (32% yield) MS (LC-MS): m / z=586, rt:5.73 min
[0631] The emission maximum of Example 1 (2 wt % in PMMA) is at 428 nm with a full width at half maximum (FWHM) of 0.27 eV. The CIE coordinate is 0.16 and the CIE coordinate is 0.08. The photoluminescence quantum yield (PLQY) is 54%.
[0632] Example 2 [ka]
[0633] Example 2 was synthesized according to General Synthetic Scheme VII by the following steps: AAV14 (33% yield): where 1,5-dibromo-2,3-dichlorobenzene (CAS: 81067-42-73) and 2,2'-dinaphthylamine (CAS: 532-18-3) are used as reactants E8 and E5, respectively. AAV15 (34% yield): where 1-(tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (CAS: 1219637-88-3) is used as reactant E3 AAV0-3 (3% yield) MS (LC-MS, APCI ion source): m / z = 786.5, rt: 7.00 min
[0634] The emission maximum of Example 2 (2 wt % in PMMA) is shown at 434 nm with a CIEx coordinate of 0.16 and a CIEy coordinate of 0.11.
[0635] Example 3 [ka]
[0636] Example 3 was synthesized according to General Synthetic Scheme III by the following steps: AAV4 (30% yield): where 5-bromo-N1,N1,N3,N3-tetraphenyl-1,3-benzenediamine (CAS: 1290039-73-4) is used as reactant E1 AAV5 (21% yield): where 6-bromo-5H-benzofuro[3,2-c]carbazole (CAS: 1438427-35-0) is used as reactant E2 AAV6 (4% yield) MS (LC-MS, APCI ion source): m / z = 676.7, rt: 6.87 min
[0637] The emission maximum of Example 3 (2 wt % in PMMA) is at 440 nm with a full width at half maximum (FWHM) of 0.21 eV. The CIE coordinate is 0.15 and the CIE coordinate is 0.06. The photoluminescence quantum yield (PLQY) is 56%.
[0638] Example 4 [ka]
[0639] Example 4 was synthesized according to General Synthetic Scheme IV by the following steps: AAV7 (71% yield): where 1-(tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (CAS: 1219637-88-3) and 3,5-dichloro-N,N-diphenylaniline (CAS: 1329428-05-8) are used as reactants E3 and E4, respectively. AAV8 (52% yield): where N,N,N'-triphenyl-benzene-1,3-diamine (CAS: 1554227-26-7) is used as reactant E5 AAV9 (3% yield) MS (LC-MS, APCI ion source): m / z = 753.9, rt: 6.62 min
[0640] The emission maximum of Example 4 (2 wt % in PMMA) is at 427 nm with a full width at half maximum (FWHM) of 0.13 eV. The CIE coordinate is 0.16 and the CIE coordinate is 0.05. The photoluminescence quantum yield (PLQY) is 58%.
[0641] Example 5 [ka]
[0642] Example 5 was synthesized according to General Synthetic Scheme V by the following steps: AAV10 (68% yield): where 2,2'-dinaphthylamine (CAS: 532-18-3) and 1-bromo-3-chlorodibenzo[b,d]furan (CAS: 2043962-13-4) are used as reactants E5 and E6, respectively. AAV11 (90% yield): where 1-(tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (CAS: 1219637-88-3) is used as reactant E3 AAV9 (38% yield) MS (LC-MS, APCI ion source): m / z = 609.5, rt: 6.26 min
[0643] The emission maximum of Example 5 (2 wt % in PMMA) is at 462 nm with a full width at half maximum (FWHM) of 0.14 eV. The CIE coordinate is 0.14 and the CIE coordinate is 0.22. The photoluminescence quantum yield (PLQY) is 65%.
[0644] Example 6 [ka]
[0645] Example 6 was synthesized by the following procedure: AAV7 (71% yield), in which 1-(tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (CAS: 1219637-88-3) and 3,5-dichloro-N,N-diphenylaniline (CAS: 1329428-05-8) were used as reactants E3 and E4, respectively. AAV12 (54% yield): where N,N'-diphenyl-m-phenylenediamine (CAS: 5905-36-2) is used as reactant E7 AAV13 (2% yield) MS (LC-MS, APCI ion source): m / z = 1094.1, rt: 8.18 min
[0646] The emission maximum of Example 6 (2 wt % in PMMA) is at 443 nm with a full width at half maximum (FWHM) of 0.13 eV. The CIE coordinate is 0.15 and the CIE coordinate is 0.07. The photoluminescence quantum yield (PLQY) is 61%.
[0647] Example 7 [ka]
[0648] Example 7 was synthesized by the following procedure: AAV16 (49% yield): where 1-(tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (CAS: 1219637-88-3) and 1,3-dibromo-2-chlorobenzene (CAS: 19230-27-4) are used as reactants E3 and E9, respectively. AAV17 (78% yield) AAV18 (56% yield): where 2,2'-dinaphthylamine (CAS: 532-18-3) was used as reactant E5; AAV19 (69% yield) AAV20 (5% yield) MS (LC-MS, AP C Ion source): m / z = 519.6, rt: 5.54 min
[0649] The emission maximum of Example 7 (2 wt % in PMMA) is at 480 nm with a full width at half maximum (FWHM) of 0.18 eV. The CIE coordinate is 0.13 and the CIE coordinate is 0.33. The photoluminescence quantum yield (PLQY) is 53%.
[0650] Example 8 [ka]
[0651] Example 8 was synthesized by the following procedure: AAV21 (85% yield): where 1-bromo-2,5-dichloro-3-fluorobenzene (CAS: 202865-57-4) and 7H-dibenzo[c,g]carbazole (CAS: 194-59-2) are used as reactants E10 and E11, respectively. AAV22 (62% yield): where 1-(tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (CAS: 1219637-88-3) is used as substrate E3 AAV23 (78% yield): where 2,4,6-trimethylphenylboronic acid (CAS: 5980-97-2) represents reactant E12 AAV0-3 (2% yield) MS (LC-MS, APCI ion source): m / z = 635.7, rt: 7.72 min
[0652] The emission maximum of Example 8 (2 wt % in PMMA) is at 470 nm with a full width at half maximum (FWHM) of 0.24 eV. The CIE coordinate is 0.15 and the CIE coordinate is 0.25. The photoluminescence quantum yield (PLQY) is 48%.
[0653] Example 9 [ka]
[0654] Example 9 was synthesized by the following procedure: AAV24 (70% yield): where 1-bromo-2-chloro-3-fluorobenzene (CAS: 883499-24-9) and 7H-dibenzo[c,g]carbazole (CAS: 194-59-2) are used as reactants E13 and E11, respectively. AAV25 (51% yield): where 1-(tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (CAS: 1219637-88-3) is used as reactant E3 AAV0-3 (2% yield) MS (LC-MS, APCI ion source): m / z = 517, rt: 6.45 min
[0655] The emission maximum of Example 9 (2 wt % in PMMA) is at 478 nm with a full width at half maximum (FWHM) of 0.26 eV. The CIE coordinate is 0.16 and the CIE coordinate is 0.36. The photoluminescence quantum yield (PLQY) is 37%.
[0656] Example 10 [ka]
[0657] Example 10 was synthesized by the following procedure: AAV21 (85% yield): where 1-bromo-2,5-dichloro-3-fluorobenzene (CAS: 202865-57-4) and 7H-dibenzo[c,g]carbazole (CAS: 194-59-2) are used as reactants E10 and E11, respectively. AAV22 (62% yield): where 1-(tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (CAS: 1219637-88-3) is used as substrate E3 AAV23 (69% yield): where phenylboronic acid (CAS: 98-80-6) represents reactant E12 AAV0-3 (1% yield) MS (LC-MS, AP C Ion source): m / z = 593, rt: 7.25 min
[0658] The emission maximum for Example 10 (2 wt % in PMMA) is shown at 485 nm.
[0659] Example 11 [ka]
[0660] Example 11 was synthesized by the following procedure: AAV26 (34% yield): where 1-bromo-3-chlorodibenzo[b,d]furan (CAS: 2043962-13-4) and 1-(tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (CAS: 1219637-88-3) are used as reactants E14 and E3, respectively. AAV27 (37% yield): where 2,2'-dinaphthylamine (CAS: 532-18-3) is used as reactant E5 AAV28 (3% yield) MS (LC-MS, AP C Ion source): m / z = 609.5, rt: 6.38 min
[0661] The emission maximum of Example 11 (2 wt % in PMMA) is at 456 nm with a full width at half maximum (FWHM) of 0.22 eV. The CIE coordinate is 0.15 and the CIE coordinate is 0.13. The photoluminescence quantum yield (PLQY) is 45%.
[0662] Example 12 [ka]
[0663] MS (LC-MS, APCI ion source): m / z = 1275.2, rt: 8.99 min The emission maximum of Example 12 (2 wt % in PMMA) is at 459 nm with a full width at half maximum (FWHM) of 0.15 eV. The CIE coordinate is 0.14 and the CIE coordinate is 0.13. The photoluminescence quantum yield (PLQY) is 53%.
[0664] Example 13 [ka] Example 13 was synthesized by the following procedure: AAV29 (71% yield): where 4-bromo-3-chlorodibenzo[b,d]furan (CAS: 1960445-63-9) and 2,2'-dinaphthylamine (CAS: 532-18-3) are used as reactants E14 and E5, respectively. AAV30 (54% yield): where 1-(tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (CAS: 1219637-88-3) is used as compound E3 AAV31 (31% yield) MS (LC-MS, APCI ion source): m / z = 609.7, rt: 6.23 min
[0665] The emission maximum of Example 13 (2 wt % in PMMA) is at 464 nm with a full width at half maximum (FWHM) of 0.13 eV. The CIE coordinate is 0.14 and the CIE coordinate is 0.18. The photoluminescence quantum yield (PLQY) is 58%.
[0666] Example 14 [ka]
[0667] Example 14 was synthesized by the following procedure: AAV32 (31% yield): where 3,6-bis(1,1-dimethylethyl)-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (CAS: 1510810-80-6) and 1,3-dibromo-5-tert-butyl-2-chlorobenzene (CAS: 1000578-25-5) are used as reactants E3 and E9, respectively. AAV33 (48% yield): where N-[1,1'-biphenyl]-4-yl-[1,1'-biphenyl]-4-amine (CAS: 102113-98-4) is used as compound E5 AAV33 (24% yield) MS (LC-MS, AP CIonization source): m / z = 740.0, rt: 7.90 min
[0668] The emission maximum of Example 14 (2 wt % in PMMA) is at 440 nm with a full width at half maximum (FWHM) of 0.22 eV. The CIE coordinate is 0.15 and the CIE coordinate is 0.06. The photoluminescence quantum yield (PLQY) is 74%.
[0669] Example 15 [ka]
[0670] Example 15 was synthesized by the following procedure: AAV38 (25% yield): where indole (CAS: 120-72-9) and 3,5-dibromobenzaldehyde (CAS: 56990-02-4) are used as reactants E17 and E18, respectively. AAV39 (51% yield): where diphenylamine (CAS: 122-39-4) is used as E19 AAV40 (38% yield) MS (LC-MS, AP C Ionization source): m / z = 1094.0, rt: 8.14 min
[0671] The emission maximum of Example 15 (2 wt % in PMMA) is at 515 nm with a full width at half maximum (FWHM) of 0.13 eV. The CIE coordinate is 0.31 and the CIE coordinate is 0.64. The photoluminescence quantum yield (PLQY) is 31%.
[0672] Example 16 [ka]
[0673] Example 16 was synthesized by the following procedure: AAV38 (25% yield): where indole (CAS: 120-72-9) and 3,5-dibromobenzaldehyde (CAS: 56990-02-4) are used as reactants E17 and E18, respectively. AAV39 (70% yield): where 2,2'-dinaphthylamine (CAS: 532-18-3) is used as E19 AAV40 (47% yield) MS (LC-MS, AP C Ionization source): m / z = 1494.0, rt: 8.74 min
[0674] The emission maximum of Example 16 (2 wt % in PMMA) is at 522 nm with a full width at half maximum (FWHM) of 0.09 eV. The photoluminescence quantum yield (PLQY) is 48%.
[0675] Example 17 [ka]
[0676] Example 17 was synthesized by the following procedure: AAV41 (34% yield): where 4,7-dihydro-1H-indole (CAS: 26686-10-2) and 3,5-dibromobenzaldehyde (CAS: 56990-02-4) are used as reactants E17 and E20, respectively. AAV42 (15% yield): where trimethyl orthoformate (CAS: 149-73-5) is used as E21 AAV43 (19% yield): where bis(3-biphenylyl)amine (CAS: 169224-65-1) is used as E19 AAV44 (27% yield) MS (LC-MS, AP C Ionization source): m / z = 988.0, rt: 8.56 min
[0677] The emission maximum of Example 17 (2 wt % in PMMA) is at 444 nm with a full width at half maximum (FWHM) of 0.29 eV. The CIE coordinate is 0.15 and the CIE coordinate is 0.09. The photoluminescence quantum yield (PLQY) is 45%.
[0678] Example 18 [ka]
[0679] Example 18 was synthesized by the following procedure: AAV45 (85% yield): where 3,6-di-tert-butylcarbazole (CAS: 37500-95-1) is used as substrate E22 AAV46 (83% yield) AAV21 (85% yield): where 1-bromo-2,5-dichloro-3-fluorobenzene (CAS: 202865-57-4) and 7H-dibenzo[c,g]carbazole (CAS: 194-59-2) are used as reactants E10 and E11, respectively. AAV22 (46% yield) AAV23 (87% yield): where 2,4,6-trimethylphenylboronic acid (CAS: 5980-97-2) represents reactant E12 AAV0-3 (7.2% yield) MS (LC-MS, APCI ion source): m / z = 746, rt: 8.90 min
[0680] The emission maximum of Example 18 (2 wt % in PMMA) is at 471 nm with a full width at half maximum (FWHM) of 0.24 eV. The CIE coordinate is 0.14 and the CIE coordinate is 0.25. The photoluminescence quantum yield (PLQY) is 48%.
[0681] Example 19 [ka]
[0682] Example 19 was synthesized by the following procedure: AAV47 (74% yield): where 4-bromo-2-chlorodibenzo[b,d]furan (CAS: 2087889-86-7) is used as substrate E14 AAV45 (85% yield): where 3,6-di-tert-butylcarbazole (CAS: 37500-95-1) is used as substrate E22 AAV48 (74% yield) AAV27 (33% yield): where bis(4-tert-butylphenyl)amine (CAS: 4627-22-9) is used as compound E5 AAV28 (6.1% yield) MS (LC-MS, AP C Ion source): m / z = 734.8, rt: 8.73 min
[0683] The emission maximum of Example 19 (2 wt % in PMMA) is at 471 nm with a full width at half maximum (FWHM) of 0.16 eV. The CIE coordinate is 0.13 and the CIE coordinate is 0.26. The photoluminescence quantum yield (PLQY) is 76%.
[0684] Example D1 Example 5 was tested on an OLED D1 fabricated with the following layer structure:
[0685] [Table 3]
[0686] [ka]
[0687] OLED D1 is 1,000 cd / m 2It has an external quantum efficiency (EQE) of 8.7% at 1,200 cd / m². The emission maximum is 466 nm at 3.9 V with a FWHM of 18 nm. The CIEx value is 0.13 and the CIEy value is 0.16. An LT95 value of 55.2 hours at 1,200 cd / m² was determined.
[0688] Additional Examples of Organic Molecules / Oligomers of the Invention [ka]
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Claims
1. An organic molecule comprising a structure represented by the following chemical formula IIIe-0: 【Chemistry 1】 In Formula IIIe-0, Q 1 is C and CR III is selected from the group consisting of Q 2 is C and CR II is selected from the group consisting of Q 3 is C and CR I is selected from the group consisting of Q 4 is C and CR 1 is selected from the group consisting of where: Q 2 and Q 3 and one or more substituents selected from the group consisting of is C; Q 2 and Q 3 When only one substituent selected from the group consisting of 1 and Q 4 and exactly one substituent selected from the group consisting of is C; R 1 , R 2 , R I, R II , R III , R IV , R V are independently selected from the group consisting of: hydrogen, deuterium, N(R 5 ) 2 、 one or more substituents R 5 C optionally substituted with 1 -C 18 alkyl, and one or more substituents R 5 C optionally substituted with 6 -C 18 aryl; R 3 is selected from C 6 -C 18 aryl optionally substituted with one or more substituents R 5 ; R a is independently selected at each occurrence from the group consisting of: hydrogen, deuterium, one or more substituents R 5 C optionally substituted with 1 -C 18 alkyl, and one or more substituents R 5 C optionally substituted with 6 -C 18 aryl; R 5 is independently selected from the group consisting of: Hydrogen, deuterium, C1-C 18 alkyl, and C 6 -C 18 aryl; the substituent R 1 is optionally linked to the substituent R 3 to form a heteroaromatic ring system; The substituent R V may optionally be, together with the substituent R 2 , 【change】 forming a heteroaromatic ring system represented by The substituent R IV optionally a substituent R V Along with 【change】 The heteroaromatic ring system represented by the formula:
2. 10. The organic molecule of claim 1 having the structure of Formula IIIe: 【Chemistry 2】 。
3. R 1 is not hydrogen, but R 1 The organic molecule of claim 1 or 2, wherein is not deuterium.
4. R V is N (R 5 ) 2 or R IV The organic molecule according to any one of claims 1 to 3, wherein the heteroaromatic ring system is selectively formed together with
5. An optoelectronic device comprising an organic molecule according to any one of claims 1 to 4 as a light emitter.
6. The optoelectronic device of claim 5, selected from the group consisting of: Organic Light Emitting Diodes (OLEDs), - light-emitting electrochemical cells, OLED sensors, - organic diodes, ・Organic solar cells, - organic transistors, - organic field effect transistors, Organic lasers and Down conversion element.
7. A composition comprising: (a) an organic molecule according to any one of claims 1 to 4 in emitter and / or host form; (b) an emitter material and / or a host material different from the organic molecule; and (c) optionally, a dye and / or a solvent.
8. An optoelectronic device comprising an organic molecule according to any one of claims 1 to 4 or a composition according to claim 7, and having the form of a device selected from the group consisting of an organic light-emitting diode (OLED), a light-emitting electrochemical cell, an OLED sensor, an organic diode, an organic solar cell, an organic transistor, an organic field-effect transistor, an organic laser and a downward conversion device.
9. -substrate, -anode, a cathode, and - comprises a light-emitting layer, the anode or the cathode is disposed on the substrate; The optoelectronic device of claim 8 , wherein the light-emitting layer is disposed between the anode and the cathode and comprises the organic molecule or the composition.
10. 10. A method for manufacturing an optoelectronic device, comprising the step of using an organic molecule according to any one of claims 1 to 4 or a composition according to claim 7, and processing said organic molecule by vacuum deposition or from solution.
Citation Information
Patent Citations
Boron containing heterocyclic compound for oleds, an organic light-emitting device, and a formulation comprising the boron-containing heterocyclic compound
US20190067577A1
Polycyclic aromatic compound
WO2012121398A1
Material for organic electroluminescent elements, organic electroluminescent element, display device, and lighting device
WO2014042197A1