Organic molecules for optoelectronic devices

Abstract

The present invention relates to an organic molecule for use in an optoelectronic device, the organic molecule having the structure of Formula I: [Formula 1] JPEG2023530344000104.jpg7689In the chemical formula I, Both T and R 1 or both V and R 1 On the other hand, R 1 Groups that are not T or V are hydrogen, deuterium, R 1 , C 1 -C 5 Alkyl, and Me, i Pr, t Ph (=phenyl), optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph, R 1 There are two R 6 , and R 6 methyl substituted with one phenyl optionally substituted with [chemical 2] JPEG2023530344000105.jpg3969 , where the dotted lines connect the positions n is an integer selected from the group consisting of 0, 1, 2, 3, 4 and 5.

Description

[Technical Field]

[0001] The present invention relates to organic light-emitting 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] The problem that the present invention aims to solve is to provide molecules that are suitable for use in optoelectronic devices. [Means for solving the problem]

[0003] Such objectives are achieved by the present invention, which provides novel organic molecules.

[0004] According to the present invention, the organic molecules are purely organic, i.e., they do not contain any metal ions, in contrast to the metal complexes known to be used in optoelectronic devices. However, the organic molecules of the present invention contain metalloids, in particular B, Si, Sn, Se and / or Ge. [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, and more preferably between 450 nm and 470 nm. The photoluminescence quantum yield of the organic molecules according to the present invention is, in particular, 50% or more. The use of the molecules according to the present invention in optoelectronic devices, such as organic light-emitting diodes (OLEDs), leads to increased device efficiency or color purity, which is expressed as the full width at half maximum (FWHM) of the device. The corresponding OLEDs have higher stability than known emitter materials and OLEDs of similar hues. DETAILED DESCRIPTION OF THE INVENTION

[0006] The organic light-emitting molecules according to the present invention comprise or consist of the structure of Formula I: [ka] In Formula I, Both of the two groups T are R 1 or both of the two groups V are R 1 On the other hand, R 1 The group T or group V, which is not hydrogen, deuterium, C1-C5 alkyl, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph; where: R 1 has the structure of the following chemical formula F: [ka] The chemical formula F is a compound consisting of two R 6 group, and n R 6 wherein n, in each occurrence, is an integer selected from the group consisting of 0, 1, 2, 3, 4, and 5; The dotted line in formula F indicates the bond position relative to the structure represented by formula I; R 6 are each independently selected from the group consisting of: hydrogen, Deuterium, and C1-C5 alkyl, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX and R X are independently selected from the group consisting of: R 1 , hydrogen, deuterium, N(R 5 )2, OR 5 , SR 5 , Si(R 5 )3. B(OR 5 )2, OSO2R 5 , CF3, CN, halogen, Optionally, one or more substituents R 5 C1-C substituted with 40 Alkyl, wherein one or more non-adjacent CH groups are optionally 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 replaced by Optionally, one or more substituents R 5 C1-C substituted with 40 Alkoxy, wherein one or more non-adjacent CH groups are optionally 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 replaced by Optionally, one or more substituents R 5 C1-C substituted with 40 thioalkoxy, wherein one or more non-adjacent CH groups are optionally 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 replaced by Optionally, one or more substituents R 5 C2-C substituted with 40 alkenyl, wherein one or more non-adjacent CH groups are optionally 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 replaced by Optionally, one or more substituents R 5 C2-C substituted with 40 Alkynyl, wherein one or more non-adjacent CH groups are optionally 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 replaced by Optionally, one or more substituents R 5 C6-C substituted with 60 aryl, and Optionally, one or more substituents R 5 C3-C substituted with 57 heteroaryl, R5 are each independently selected from the group consisting of: Hydrogen, deuterium, OPh (Ph = phenyl), SPh, CF3, CN, F, Si(C1-C5 alkyl)3, Si(Ph)3, C1-C5 alkyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF3 or F; C1-C5 alkoxy, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF3 or F; C1-C5 thioalkoxy, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF3 or F; C2-C5 alkenyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF3 or F; C2-C5 alkynyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF3 or F; C6-C optionally substituted with one or more C1-C5 alkyl substituents 18 aryl, C3-C optionally substituted with one or more C1-C5 alkyl substituents 17 heteroaryl, N(C6-C 18 aryl)2, N(C3-C 17 heteroaryl)2, and N(C3-C 17 Heteroaryl)(C6-C 18 aryl), R XI is selected from the group consisting of hydrogen, chlorine and C1-C5 alkyl.

[0007] According to the present invention, both of the two groups T are R 1 or both of the two groups V are R 1 All variables T and V in formula I are R 1It is not something that is.

[0008] That is, the organic molecules of the present invention comprise or consist of a structure selected from the group consisting of Formula Ia and Formula Ib:

[0009] [ka] In formula Ia: V # is selected from the group consisting of: hydrogen, deuterium, C1-C5 alkyl, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0010] [ka] In formula Ib: T # is selected from the group consisting of: hydrogen, deuterium, C1-C5 alkyl, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph. According to the present invention, R 1 is attached via the dotted line shown in formula F, which is similar to formula Ia shown below: [ka]

[0011] It is meant that Formula Ib may be represented similarly as follows: [ka]

[0012] Organic molecules of the invention have two or more groups having the structure of formula F, but can have up to 12 groups having the structure of formula F. Particular embodiments of organic molecules have two or four groups having the structure of formula F.

[0013] In a preferred embodiment, the organic molecule comprises or consists of a structure selected from the group consisting of Formula Ia and Formula Ib, wherein T # and V # is selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0014] In a preferred embodiment, T and V are selected from the group consisting of: R 1 , Hydrogen, deuterium, Me, i Pr, t Bu, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0015] Depending on the value of the integer n, R 1 can have the following structure:

[0016] If n=0, [ka] ,

[0017] When n=1, [ka]

[0018] When n=2, [ka]

[0019] When n=3, [ka]

[0020] When n=4, [ka]

[0021] When n=5, [ka]

[0022] where R 6 are, each occurrence independently of each other, selected from the group consisting of hydrogen, deuterium, and C1-C5 alkyl, wherein in certain embodiments, the C1-C5 alkyl group is selected from Me, i Pr, t Also Bu or neo-pentyl.

[0023] In certain embodiments, R 6 are in each case, independently of one another, hydrogen, deuterium, Me, i Pr, t It is selected from the group consisting of Bu and neo-pentyl.

[0024] In other embodiments, R 6 are each independently selected from the group consisting of hydrogen and Me.

[0025] In a preferred embodiment, R 1 In each case, the chemical formula R 1a and chemical formula R 1b is selected from the group consisting of:

[0026] [ka]

[0027] [ka]

[0028] R 1 Specific examples include: [ka]

[0029] In a particularly preferred embodiment, R 1 is the chemical formula R 1c and chemical formula R 1d is selected from the group consisting of:

[0030] [ka]

[0031] [ka] In one embodiment, R XI is hydrogen, Me, i Pr and t Bu.

[0032] In one embodiment, R XI is selected from the group hydrogen or Me.

[0033] In one embodiment, R XI is hydrogen.

[0034] In one embodiment, R XI is chlorine.

[0035] In one embodiment, RXI is Me.

[0036] In one embodiment of the organic molecule, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX and R X are independently selected from the group consisting of: R 1 , Hydrogen, deuterium, halogens, Me, i Pr, t Bu, CN, CF3, SiMe3, SiPh3, 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; N(Ph)2. In one embodiment, R I , R II , R III , R IV , R V , R VI , RVII , R VIII , R IX and R X are independently selected from the group consisting of: R 1 , Hydrogen, deuterium, halogens, 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; N(Ph)2.

[0037] In one embodiment, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX and R X are independently selected from the group consisting of: R 1 , hydrogen, deuterium, halogen, Me, i Pr, tBu, 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 triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; N(Ph)2.

[0038] In one embodiment, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX and R X are independently selected from the group consisting of: R 1 , hydrogen, deuterium, 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, t carbazolyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3 and Ph; and N(Ph)2.

[0039] In one embodiment, RI , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX and R X are independently selected from the group consisting of: R 1 , hydrogen, deuterium, 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 N(Ph)2.

[0040] In one embodiment, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX and R X are independently selected from the group consisting of: R 1 , hydrogen, deuterium, 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 N(Ph)2.

[0041] In one embodiment, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX and R X is R 1 ,hydrogen, tare independently selected from the group consisting of Bu and Ph.

[0042] In one embodiment of the present invention, R X =R I , R IX =R II , R VIII =R III , R VII =R IV , and R V =R VI which produces an organic molecule comprising or consisting of the structure of Formula II:

[0043] [ka]

[0044] In one embodiment, the organic molecule comprises or consists of the structure of Formula II, where R I , R II , R III , R IV and R V are independently selected from the group consisting of: R 1 , Hydrogen, deuterium, halogens, Me, i Pr, t Bu, CN, CF3, SiMe3, SiPh3, 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, tcarbazolyl 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; N(Ph)2.

[0045] In one embodiment, the organic molecule comprises or consists of Formula II, where R I , R II , R III , R IV and R V are independently selected from the group consisting of: R 1 , Hydrogen, deuterium, halogens, 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; N(Ph)2.

[0046] In one embodiment, the organic molecule comprises or consists of Formula II, where R I , R II , R III , R IV and R V are independently selected from the group consisting of: R 1 , Hydrogen, deuterium, halogens, 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 triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; N(Ph)2.

[0047] In one embodiment, the organic molecule comprises or consists of Formula II, where R I , R II , R III , R IV and R V are independently selected from the group consisting of: R 1 , hydrogen, deuterium, Me, i Pr, t Bu, Me, i Pr, tPh optionally substituted with one or more substituents independently selected from the group consisting of Bu 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; and N(Ph)2.

[0048] In one embodiment, the organic molecule comprises or consists of Formula II, where R I , R II , R III , R IV and R V are independently selected from the group consisting of: R 1 , hydrogen, deuterium, 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 N(Ph)2.

[0049] In one embodiment, the organic molecule comprises or consists of Formula II, where R I , R II , R III , R IV and R V are independently selected from the group consisting of: R 1 , hydrogen, deuterium, 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 N(Ph)2.

[0050] In one embodiment, the organic molecule comprises or consists of Formula II, where R I , R II, R III , R IV and R V is R 1 ,hydrogen, t are independently selected from the group consisting of Bu and Ph.

[0051] In one embodiment, the organic molecule comprises or consists of a structure selected from the group consisting of Formula II-1 and Formula II-2:

[0052] [ka]

[0053] [ka]

[0054] Examples of organic molecules according to the present invention that comprise or consist of a structure selected from the group consisting of Formula II-1 and Formula II-2:

[0055] [ka]

[0056] [ka]

[0057] In certain embodiments of the present invention, the organic molecule comprises or consists of a structure selected from the group consisting of Formula IIa, Formula IIb, Formula IIc, and Formula IId: [ka]

[0058] [ka]

[0059] [ka]

[0060] [ka]

[0061] Examples of organic molecules comprising or consisting of a structure selected from the group consisting of Formula IIa, Formula IIb, Formula IIc, and Formula IId are as follows: [ka]

[0062] In one embodiment, the organic molecule comprises or consists of a structure selected from the group consisting of Formula IIIa and Formula IIIb: [ka]

[0063] [ka]

[0064] In a preferred embodiment, the organic molecule comprises or consists of a structure selected from the group consisting of Formula IIIa-1 and Formula IIIb-1: [ka]

[0065] [ka]

[0066] In one embodiment, the organic molecule comprises or consists of a structure selected from the group consisting of Formula IV-1 and Formula IV-2:

[0067] [ka]

[0068] [ka]

[0069] In one embodiment, the organic molecule comprises or consists of a structure selected from the group consisting of Formula IVa and Formula IVb: [ka]

[0070] [ka]

[0071] In one embodiment, the organic molecule comprises or consists of a structure selected from the group consisting of formula IV-3 and formula IV-4. [ka]

[0072] [ka]

[0073] In one embodiment, the organic molecule comprises or consists of a structure selected from the group consisting of Formula IVc and Formula IVd. [ka]

[0074] [ka]

[0075] As used throughout this specification, the terms "aryl" and "aromatic" are understood in the broadest sense to refer to any monocyclic, bicyclic, or polycyclic aromatic moiety. Thus, an aryl group contains 6 to 60 aromatic ring atoms. A heteroaryl group contains 5 to 60 aromatic ring atoms, at least one of which is a heteroatom. Nevertheless, throughout this specification, the number of aromatic ring atoms may be given in subscript numerals in the definitions of specific substituents. In particular, heteroaromatic rings contain 1 to 3 heteroatoms. Furthermore, the terms "heteroaryl" and "heteroaromatic" are understood in the broadest sense to refer to any monocyclic, bicyclic, or polycyclic heteroaromatic moiety containing at least one heteroatom, which in each case may be the same or different and may be independently selected from the group consisting of N, O, and S. Thus, the term "arylene" refers to a divalent substituent that possesses two binding sites and serves as a linker structure for other molecular structures. In exemplary embodiments, if a group is defined differently from the definitions given herein, for example, if the number of aromatic ring atoms or heteroatoms differs from the definitions given, the definition in the exemplary embodiment applies. According to the present invention, a fused (annulated) aromatic or heteroaromatic polycycle is composed of two or more single aromatic or heteroaromatic rings that form the polycycle via a condensation reaction.

[0076] In particular, as used throughout this specification, the term "aryl group" or "heteroaryl group" includes 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, naphthoimidazole, phenanthridine, pyridoimidazole ... and 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 a group that can be attached through any position of an aromatic or heteroaromatic group derived from a combination of the aforementioned groups.

[0077] As used throughout this specification, the term "cyclic group" is understood in the broadest sense as any monocyclic, bicyclic or polycyclic moiety.

[0078] As used throughout this specification, the term "biphenyl" is also understood in its broadest sense as a substituent to refer to ortho-biphenyl, meta-biphenyl, or para-biphenyl, where ortho, meta, and para are defined in relation to the point of attachment to another chemical moiety.

[0079] As used throughout this specification, the term "alkyl group" is understood in the broadest sense to include any linear, branched, or cyclic alkyl substituent. In particular, the term "alkyl" includes the substituents methyl (Me), ethyl (Et), n-propyl (N-propyl), ... ethyl (Et), n-propyl (N-propyl), methyl (Me), ethyl (Et), ethyl (Et), propyl (Et), propyl (Et), propyl (Et), propyl (Et), propyl (Et), propyl (Et n Pr), i-propyl ( i Pr), cyclopropyl, n-butyl ( n Bu), i-butyl ( i Bu), s-butyl ( s Bu), t-butyl ( tBu), 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-methylcyclohexyl, 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- 1,1-dimethyl-n-dodec-1-yl, 1,1-dimethyl-n-tetradec-1-yl, 1,1-dimethyl-n-hexadece-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-dodec- 1-yl, 1,1-diethyl-n-tetradec-1-yl, 1,1-diethyl-n-hexadece-1-yl, 1,1-diethyl-n-octadec-1-yl, 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.

[0080] As used throughout this specification, the term "alkenyl" includes linear, branched, and cyclic alkenyl substituents. The term "alkenyl group" includes, for example, the substituents ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, or cyclooctadienyl.

[0081] As used throughout this specification, the term "alkynyl" includes linear, branched and cyclic alkynyl substituents. The term "alkynyl group" includes, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl.

[0082] As used throughout this specification, the term "alkoxy" includes linear, branched, and cyclic alkoxy substituents. The term "alkoxy group" includes, for example, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, and 2-methylbutoxy.

[0083] The term "thioalkoxy" as used throughout this specification includes linear, branched and cyclic thioalkoxy substituents, where O in the exemplary alkoxy group is replaced with S.

[0084] The terms "halogen" and "halo" as used throughout this specification are also understood in the broadest sense, preferably fluorine, chlorine, bromine or iodine.

[0085] Wherever hydrogen (H) is mentioned herein, it is also substituted with deuterium in each instance.

[0086] When a molecular fragment is described as being attached to a substituent or other moiety, the name may be described as just the fragment (e.g., naphthyl, dibenzofuryl) or as the whole molecule (e.g., naphthalene, dibenzofuran). As used herein, the above ways of describing a substituent or attached fragment are considered equivalent.

[0087] In one embodiment, in a poly(methyl methacrylate) (PMMA) film containing 2 wt. % organic molecules at room temperature, the organic molecules according to the present invention have an excited state lifetime of 150 μs or less, 100 μs or less, particularly 50 μs or less, more preferably 10 μs or less.

[0088] In a further embodiment of the present invention, in a PMMA film containing 2 wt. % of organic molecules at room temperature, the organic molecules according to the present invention have an emission peak in the visible or near-ultraviolet range, i.e., in the wavelength range of 380-800 nm, with a full width at half maximum value of less than 0.23 eV, preferably less than 0.20 eV, more preferably less than 0.19 eV, even more preferably less than 0.18 eV or even less than 0.17 eV.

[0089] Orbital energies and excited state energies can be determined through experimental methods. The highest occupied molecular orbital energy, E HOMO is determined to an accuracy of 0.1 eV from cyclic voltammetry measurements by methods known to those skilled in the art. LUMO is E HOMO +E gap where E gap is determined as follows: for host compounds, unless otherwise specified, the onset of the emission spectrum of a 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 containing 10% by weight of the emitter intersect. For the organic molecules according to the present invention, E gap is determined as the energy at which the excitation and emission spectra of a PMMA film containing 2 wt. % of the emitter intersect.

[0090] 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 in which the first excited singlet state and the lowest triplet state are energetically separated by 0.4 eV or more, phosphorescence is typically visible in the steady-state spectrum in 2-Me-THF. Therefore, the triplet energy is also determined as 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, measured in a PMMA film containing 10 wt. % of the emitter, unless otherwise specified, and for organic molecules according to the present invention, measured in a PMMA film containing 2 wt. % of the organic molecules according to the present invention. For both host and emitter compounds, the energy of the first excited singlet state S1 is determined from the onset of the emission spectrum and, unless otherwise specified, is measured in a PMMA film containing 10 wt. % of the host or emitter compound, or in the case of organic molecules according to the invention, in a PMMA film containing 2 wt. % of organic molecules according to the invention.

[0091] The onset of the emission spectrum is determined by calculating the intersection of a tangent to the emission spectrum with the x-axis, which is set at the high energy side of the emission band and at half maximum of the maximum intensity of the emission spectrum.

[0092] In one embodiment, the organic molecules according to the present invention have, in a PMMA film comprising 2 wt. % of the organic molecules at room temperature, an onset of the emission spectrum that is energetically close to the emission maximum, i.e. the energy difference between the onset of the emission spectrum and the energy of the emission maximum is less than 0.14 eV, preferably less than 0.13 eV, or even more preferably less than 0.12 eV, and the full width at half maximum (FWHM) of said organic molecules is less than 0.23 eV, preferably less than 0.20 eV, more preferably less than 0.19 eV, even more preferably less than 0.18 eV, or even more preferably less than 0.17 eV, resulting in a CIE y coordinate of less than 0.20, preferably less than 0.18, or even more preferably less than 0.16 or less than 0.14.

[0093] A further aspect of the present invention relates to the use of organic molecules according to the 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.

[0094] A preferred embodiment relates to the use of organic molecules according to the invention as light emitters in optoelectronic devices.

[0095] An optoelectronic device is understood in the broadest sense as any device based on organic materials that is suitable for emitting light in the visible or near ultraviolet (UV) range, i.e., in the wavelength range of 380 to 800 nm, and more preferably, the optoelectronic device is capable of emitting light in the visible range, i.e., in the wavelength range of 400 to 800 nm.

[0096] In connection with such applications, the optoelectronic device is more particularly selected from the group consisting of: Organic Light-Emitting Diode (OLED) Light-emitting electrochemical cells OLED sensors, especially gas and vapor sensors that are not completely isolated from the outside Organic diodes ·Organic solar cells Organic transistors Organic field-effect transistors Organic laser Downward conversion element For such applications, in preferred embodiments, 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.

[0097] For said applications, the fraction of the organic molecules according to the invention in the light-emitting layer in an optoelectronic device, more particularly in an OLED, is 0.1% to 99% by weight, more particularly 1% to 80% by weight. In another embodiment, the proportion of the organic molecules in the light-emitting layer is 100% by weight.

[0098] In one embodiment, the emissive layer comprises not only the 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 of the organic molecule.

[0099] A further aspect of the present invention relates to a composition comprising or consisting of: (a) one or more organic molecules according to the invention in emitter and / or host form; (b) one or more emitter and / or host materials different from the organic molecules according to the invention, and (c) optionally, one or more dyes and / or one or more solvents.

[0100] In one embodiment, the light-emitting layer comprises or consists essentially of a composition comprising or consisting of: (a) one or more organic molecules according to the invention in emitter and / or host form; (b) one or more emitter and / or host materials different from the organic molecules according to the invention, and (c) optionally, one or more dyes and / or one or more solvents.

[0101] In particular embodiments, the emissive layer EML comprises or consists essentially of a composition comprising or consisting of: (i) 0.1 to 10% by weight, preferably 0.5 to 5% by weight, in particular 1 to 3% by weight, of one or more organic molecules according to the invention, (ii) 5 to 99% by weight, preferably 15 to 85% by weight, in particular 20 to 75% by weight, of one or more host compounds H, (iii) 0.9 to 94.9% by weight, preferably 14.5 to 80% by weight, in particular 24 to 77% by weight, of one or more additional host compounds D having a structure different from that of the molecules according to the invention, (iv) optionally 0 to 94% by weight, preferably 0 to 65% by weight, in particular 0 to 50% by weight, of a solvent, and (v) optionally 0 to 30% by weight, in particular 0 to 20% by weight, preferably 0 to 5% by weight, of at least one additional emitter molecule F having a structure different from that of the molecule according to the invention.

[0102] Preferably, energy is transferred from the host compound H to one or more organic molecules according to the 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 E according to the invention and / or from the first excited singlet state S1(H) of the host compound H to the first excited singlet state S1(E) of one or more organic molecules E according to the invention.

[0103] In one embodiment, the host compound H has an energy E in the range of −5 to 6.5 eV. HOMO (H), and at least one additional host compound D has a highest occupied molecular orbital HOMO (H) with energy E HOMO (D) has the highest occupied molecular orbital HOMO (D), where E HOMO (H)>E HOMO (D).

[0104] In a further embodiment, the host compound H has an energy E LUMO(H), and at least one additional host compound D has 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).

[0105] 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), At least one additional host compound D has an energy E HOMO (D) has the 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 The highest occupied molecular orbital (HOMO) with (E), and energy E LUMO (E) having a 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, more preferably −0.3 eV to 0.3 eV, even more preferably −0.2 eV to 0.2 eV, or even more preferably −0.1 eV to 0.1 eV, E LUMO (H)>E LUMO (D), and the energy level of the lowest unoccupied molecular orbital (LUMO) (E) of the organic molecule E according to the present invention (E LUMO (E)) and the energy level of the lowest unoccupied molecular orbital (LUMO) (D) of at least one additional host compound D (E LUMOThe difference from (D)) is −0.5 eV to 0.5 eV, more preferably −0.3 eV to 0.3 eV, even more preferably −0.2 eV to 0.2 eV, or even more preferably −0.1 eV to 0.1 eV.

[0106] In one embodiment of the present invention, the host compound D and / or the host compound H is a thermally activated delayed fluorescence (TADF) material. The TADF material has a wavelength of 2500 cm -1 ΔE corresponds to the energy difference between the first excited singlet state (S1) and the first excited triplet state (T1) less than ST Preferably, the TADF material has a 3000 cm -1 less than 1500 cm -1 less than, even more preferably, 1000 cm -1 Less than, or more preferably, 500 cm -1 Less than ΔE ST Indicates the value.

[0107] In one embodiment, host compound D is a TADF material and host compound H is a TADF material having a luminescence wavelength of 2500 cm -1 Larger ΔE ST In certain embodiments, host compound D is a TADF material and host compound H is selected from the group consisting of 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.

[0108] In one embodiment, host compound H is a TADF material and host compound D is a TADF material having a luminescence wavelength of 2500 cm -1 Larger ΔE STIn 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).

[0109] In a further aspect, the present invention relates to an optoelectronic device comprising an organic molecule or composition of the type described herein, more particularly a device selected from the group consisting of an organic light emitting diode (OLED), a light emitting electrochemical cell, an OLED sensor, in particular a gas sensor and a vapor sensor that are not completely sealed off from the outside, an organic diode, an organic solar cell, an organic transistor, an organic field effect transistor, an organic laser, and a downward conversion device.

[0110] 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.

[0111] In one embodiment of the optoelectronic device of the present invention, the organic molecule E according to the present invention is used as emissive material in the emissive layer EML.

[0112] 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 as described herein.

[0113] 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 Here, the OLED optionally includes layers selected from the group consisting of HIL, HTL, EBL, HBL, ETL, and EIL, and different layers are combined, and the OLED also includes one or more layers of each layer type defined above. Additionally, the optoelectronic device, in one embodiment, also includes at least one protective layer that protects the device from damaging exposure to harmful substances in the environment, including, for example, moisture, vapors and / or gases.

[0114] 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 Here, the OLED optionally includes layers selected from the group consisting of HIL, HTL, EBL, HBL, ETL, and EIL, and different layers are combined, and the OLED also includes one or more layers of each layer type defined above.

[0115] In one embodiment of the present invention, the optoelectronic device is an OLED that can have a stacked structure. In this structure, individual units are stacked on top of each other, unlike the typical side-by-side arrangement of OLEDs. Mixed light is generated by an OLED that exhibits a stacked structure, and in particular, white light is generated by stacking a blue OLED, a green OLED, and a red OLED. An OLED that exhibits a stacked structure may also include a charge generation layer (CGL), which is typically located between two OLED subunits and typically configured as an n-doped layer and a p-doped layer. Typically, the n-doped layer of one CGL is located closer to the anode layer.

[0116] 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. In particular, a so-called tandem OLED comprises three emissive layers, where one light-emitting layer emits red light, one light-emitting layer emits green light, and one light-emitting layer emits blue light. Optionally, additional layers such as charge generation layers, charge blocking layers, or charge transport layers may be included between the individual light-emitting layers. In a further embodiment, the light-emitting layers are stacked adjacently. In a further embodiment, the tandem OLED comprises a charge generation layer between each two light-emitting layers. Adjacent light-emitting layers or light-emitting layers separated by a charge generation layer may also be combined.

[0117] The substrate can be made of any material or composition of materials. Most often, a glass slide is used as the substrate. Alternatively, a thin metal layer (e.g., copper, gold, silver, or aluminum film) or a plastic film or slide can be used, which allows for a higher level of flexibility. The anode layer A is made of a material that allows for a nearly (essentially) transparent film. To allow light emission from the OLED, at least one of the two electrodes must be (essentially) transparent, so either the anode layer A or the cathode layer C is transparent. Preferably, the anode layer A is rich in or consists of transparent conductive oxides (TCOs). Such anode layers A may, for example, comprise 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.

[0118] 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 due to the transparent conductive oxide (TCO) can also be reduced by using a hole injection layer (HIL). The HIL also facilitates the injection of like charge carriers (i.e., holes) in that the transport of like charge carriers from the TCO to the hole transport layer (HTL) is promoted. The hole injection layer (HIL) can also include poly-3,4-ethylenedioxythiophene (PEDOT), polystyrene sulfonate (PSS), MoO2, VO5, CuPC, or CuI, particularly a mixture of PEDOT and PSS. The hole injection layer (HIL) can also prevent metal diffusion from the anode layer A to the hole transport layer (HTL). For example, the HIL may be poly-3,4-ethylenedioxythiophene:polystyrenesulfonic acid (PEDOT: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′-diyl)bis(N1-phenyl-N4,N4-di-m-tolylbenzene-1,4-diamine (DNTPD), N,N′-bis(1-naphthyl)-(2 ... It may also be composed of N,N'-triphenyl-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine (NPB), N,N'-diphenyl-N,N'-di-[4-(N,N-diphenylamino)phenyl]benzidine (NPNPB), N,N,N',N'-tetrakis(4-methoxyphenyl)benzidine (MeO-TPD), 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN) and / or N,N'-diphenyl-N,N'-bis-(1-naphthyl)-9,9'-spirobifluorene-2,7-diamine (Spiro-NPD).

[0119] The hole transport layer (HTL) is generally 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 also 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) can also function 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) may be formed of tris(4-carbazolyl-9-ylphenyl)amine (TCTA), poly(4-butylphenyl-diphenylamine) (poly-TPD), poly(4-butylphenyl-diphenylamine) (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 9,9′-diphenyl-6-(9-phenyl-9H- The HTL may also include a star-shaped heterocycle such as (carbazol-3-yl)-9H,9'H-3,3'-bicarbazole (TrisPcz). The HTL may also include a p-doped layer composed of an inorganic or organic dopant in an organic hole-transporting matrix. The inorganic dopant may be, for example, a transition metal oxide such as vanadium oxide, molybdenum oxide, or tungsten oxide. The organic dopant may be, for example, tetrafluorotetracyanoquinodimethane (F4-TCNQ), copper-pentafluorobenzoate (Cu(I)pFBz), or a transition metal complex.

[0120] 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).

[0121] The light-emitting layer (EML) is generally located adjacent to the hole-transporting layer (HTL). The light-emitting layer (EML) comprises at least one light-emitting molecule. In particular, the EML comprises one or more light-emitting molecules E according to the present invention. In one embodiment, the light-emitting layer comprises only organic molecules according to the present invention. Typically, the EML further comprises one or more host materials H. For example, the host material H may 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), 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenz ...

[0033] The compound is selected from the group consisting of 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzothiophen-2-yl)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 a first triplet (T1) energy level and a first singlet (S1) energy level that are energetically higher than the first triplet (T1) energy level and the first singlet (S1) energy level of the organic molecule.

[0122] 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 embodiment, the EML comprises exactly one light-emitting organic molecule according to the present invention, T2T as the electron-dominant host, and one 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 as the hole-dominant host. In a further embodiment, the EML comprises 50 to 80% by weight, preferably 60 to 75% by weight, 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 to 45% by weight, preferably 15 to 30% by weight, of T2T, and 5 to 40% by weight, preferably 10 to 30% by weight, of an emissive molecule according to the present invention.

[0123] An electron transport layer (ETL) may be located 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 can also be doped with a material such as Liq. The electron transport layer (ETL) can also block holes, or a hole blocking layer (HBL) can be introduced.

[0124] Examples of HBL include 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline = bathocuproine (BCP), 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. These include 2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine (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).

[0125] Adjacent to the electron transport layer (ETL) may be a cathode layer C. 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 C may also consist of an (essentially) opaque metal such as Mg, Ca, or Al. Alternatively, the cathode layer C may also comprise graphite and / or carbon nanotubes (CNTs). Alternatively, the cathode layer C may also consist of nanoscale silver wires.

[0126] The OLED optionally further includes a protective layer (also referred to as an electron injection layer (EIL)) between the electron transport layer (ETL) and the cathode layer C. The layer may include lithium fluoride, cesium fluoride, silver, 8-hydroxyquinolinolatolithium (Liq), Li2O, BaF2, MgO, and / or NaF.

[0127] Optionally, the electron transporting layer (ETL) and / or the hole blocking layer (HBL) also comprise one or more host compounds H. The emitting layer EML may further include one or more additional emitter molecules F to further modify the emission spectrum and / or absorption spectrum of the emitting layer EML. Such emitter molecules F may be any emitter molecule known in the art. Preferably, such emitter molecules F are molecules having 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 optionally be fluorescent and / or phosphorescent emitter molecules capable of shifting the emission spectrum and / or absorption spectrum of the emitting layer EML. For example, triplet and / or singlet excitons may be transferred from the emitter molecules according to the present invention to the emitter molecules F before relaxing to the ground state S, typically emitting red-shifted light compared to the light emitted by the organic molecules. Optionally, the emitter molecules F may also induce a two-photon effect (i.e., absorption of two photons at half the maximum absorption energy).

[0128] Optionally, the optoelectronic device (e.g., OLED) may also be, for example, essentially a white optoelectronic device. For example, such a white optoelectronic device may comprise at least one (deep) blue emitter molecule and one or more emitter molecules that emit green and / or red light. Optionally, there may then be energy transfer between the two or more molecules, as described above.

[0129] 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 >380~420nm Deep blue: wavelength range of >420~480nm Sky blue: wavelength range of >480~500nm Green: wavelength range of >500~560nm Yellow: wavelength range of >560-580nm Orange: wavelength range of >580~620nm Red: wavelength range of >620~800nm Associated with the emitter molecule, such hues exhibit emission maxima. Thus, for example, a deep blue emitter has an emission maximum in the >420-480 nm range, a sky blue emitter has an emission maximum in the >480-500 nm range, a green emitter has an emission maximum in the >500-560 nm range, and a red emitter has an emission maximum in the >620-800 nm range.

[0130] The deep blue emitter may preferably have a maximum emission of less than 480 nm, more preferably less than 470 nm, even more preferably less than 465 nm, or even more preferably less than 460 nm. The maximum emission is typically greater than 420 nm, preferably greater than 430 nm, more preferably greater than 440 nm, or even more preferably greater than 450 nm.

[0131] Therefore, a further aspect of the present invention is 2 an OLED that exhibits an external quantum efficiency of greater than 8%, preferably greater than 10%, more preferably greater than 13%, even more preferably greater than 15%, or even more preferably greater than 20% at 420 nm to 500 nm, preferably 430 nm to 490 nm, more preferably 440 nm to 480 nm, and even more preferably 450 nm to 470 nm; and / or an OLED that exhibits an external quantum efficiency of greater than 500 cd / m 2 and OLEDs exhibiting an LT80 value of greater than 100 h, preferably greater than 200 h, more preferably greater than 400 h, even more preferably greater than 750 h, or even more preferably greater than 1000 h. Accordingly, a further aspect of the present invention relates to OLEDs exhibiting a CIEy color coordinate of emission less than 0.45, preferably less than 0.30, more preferably less than 0.20, even more preferably less than 0.15, or even more preferably less than 0.10.

[0132] Yet another aspect of the present invention relates to OLEDs that emit light at well-defined color points. According to the present invention, the OLEDs emit light with a narrow emission bandwidth (small full width at half maximum (FWHM)). In one aspect, the OLEDs according to the present invention emit light with an FWHM of the main emission peak of less than 0.30 eV, preferably less than 0.25 eV, more preferably less than 0.20 eV, even more preferably less than 0.19 eV, or even more preferably less than 0.17 eV.

[0133] Yet another aspect of the present invention relates to an OLED that emits light having CIEx and CIEy color coordinates close to the CIEx (=0.131) and CIEy (=0.046) color coordinates of primary blue (CIEx=0.131 and CIEy=0.046) as defined by ITU-R Recommendation BT.2020 (Rec.2020), which is suitable for use in UHD (Ultra High Definition) displays, such as UHD-TVs. Thus, a further 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 even 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 even more preferably 0.04 to 0.10.

[0134] In a further aspect, the present invention relates to a method for producing an optoelectronic component, in which the organic molecule of the present invention is used.

[0135] The optoelectronic device, in particular the OLED according to the present invention, may be produced by any means of vapor deposition and / or liquid processes. Thus, at least one layer may be - Produced by the sublimation process; - Manufactured by organic vapor phase deposition process, - Produced by a carrier gas sublimation process, - Solution processed or printed.

[0136] The methods used to manufacture optoelectronic devices, and in particular 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 can be deposited using the same or different deposition methods.

[0137] For example, vapor deposition processes include thermal (co)evaporation, chemical vapor deposition, and physical vapor deposition. In the case of active matrix OLED displays, an AMOLED backplane is used as the substrate. Individual layers can also be processed from solutions or dispersions using appropriate solvents. For example, solution deposition processes include spin coating, dip coating, and jet printing. Solution processing is optionally performed in an inert atmosphere (e.g., nitrogen atmosphere), and the solvent is completely or partially removed by means known in the art. [Example]

[0138] General Synthesis Method I The general synthesis method is X =R I , R IX =R II , R VIII =R III , R VII =R IV and R V =R VI A synthetic scheme is provided for an organic molecule according to the present invention, which is:

[0139] [ka]

[0140] Alternatively, trimethylborate can be used as the boronating reagent to generate the corresponding boronic acid derivative of I3. [ka]

[0141] Alternatively, the boronic acid derivative corresponding to substrate I3 can be used as the starting material under the same conditions.

[0142] Another one-pot ring closure method for the direct conversion of I2 to P1. [ka]

[0143] General procedure for synthetic AAV1 [ka]

[0144] E1 (1.00 equivalents), E2 (1.10 equivalents), tris(dibenzylideneacetone)dipalladium Pd2(dba)3 (0.01 equivalents, CAS: 51364-51-3), tri-tert-butylphosphine (P( t Bu)3, CAS: 13716-12-6, 0.04 equivalents) and sodium tert-butoxide (NaO t Bu (1.70 equiv.) is stirred in toluene under a nitrogen atmosphere at 80 °C for 1-16 h. After cooling to room temperature (rt), the reaction mixture is extracted with toluene and water, and the phases are separated. The combined organic layers are dried over MgSO4, and the solvent is removed under reduced pressure. The resulting crude product is purified by recrystallization or column chromatography to give I1 as a solid or oil.

[0145] General procedure for synthetic AAV2 [ka] I1 (2.20 equiv.), E3 (1.00 equiv.), tris(dibenzylideneacetone)dipalladium Pd2(dba)3 (0.02 equiv., CAS: 51364-51-3), tri-tert-butylphosphine (0.08 equiv., P( tBu)3, CAS: 13716-12-6) and sodium tert-butoxide (NaO t Bu (3.30 equiv.) is stirred in toluene under a nitrogen atmosphere at 110 °C for 1-16 h. After cooling to room temperature (rt), the reaction mixture is extracted with toluene and water, and the phases are separated. The combined organic layers are dried over MgSO4, and the solvent is removed under reduced pressure. The resulting crude product is purified by recrystallization or column chromatography to give I2 as a solid.

[0146] General procedure for synthetic AAV3 [ka] Under a nitrogen atmosphere, I2 (1.00 equiv.) is dissolved in dry THF. The resulting solution is cooled to -10 °C. Then, tert-BuLi (2.20 equiv., CAS: 594-19-4) is slowly added and stirring is continued at 0 °C. After complete lithiation, 1,3,2-dioxaborolane (3.00 equiv., CAS: 61676-62-8, or alternatively, trimethylborate, CAS 121-43-7) is added, followed by heating at 40 °C for 2 h. After cooling to room temperature (rt), water is added and the phases are separated. The combined organic layers are dried over MgSO4, filtered, and concentrated under reduced pressure. The resulting crude product is purified by recrystallization or column chromatography to give I3 or the corresponding boronic acid, respectively, as a solid.

[0147] General procedure for synthetic AAV4 [ka] I3 (1.00 equiv.), N,N-diisopropylethylamine (10 equiv., CAS: 7087-68-5), and AlCl3 (10 equiv., CAS: 7446-70-0) are stirred in chlorobenzene under a nitrogen atmosphere at 120 °C for 4 h. After cooling to room temperature (rt), the reaction mixture is extracted with toluene and water, and the phases are separated. The combined organic layers are dried over MgSO4, and the solvent is removed under reduced pressure. The resulting crude product is purified by recrystallization or column chromatography to give P1 as a solid.

[0148] General procedure for synthetic AAV5 [ka]

[0149] I2 (1.00 equivalents) is dissolved in tert-butylbenzene under a nitrogen atmosphere and the solution is cooled to -30 °C. t BuLi) solution (2.20 equiv., CAS: 594-19-4) is added dropwise and the reaction mixture is allowed to warm to 0° C. After stirring at 60° C. for 120 min, t The solvent and by-products of the BuLi solution are removed under reduced pressure, and the reaction mixture is cooled again to -30 °C. Boron tribromide solution (BBr3, CAS: 10294-33-4, 2.20 equiv.) is added dropwise, the cooling bath is removed, and the reaction mixture is allowed to warm to room temperature (rt). After stirring at room temperature for 30 minutes, the reaction mixture is cooled to 0 °C, and N,N-diisopropylethylamine (CAS: 7087-68-5, 3.00 equiv.) is added. After warming to room temperature, the reaction mixture is heated to reflux at 120 °C for 3 hours. The reaction mixture is then poured into water, and the resulting precipitate is filtered and washed with a minimum amount of ethyl acetate to give P1 as a solid product. P1 can be further purified by recrystallization or flash chromatography.

[0150] General Synthesis Method II The general synthesis method II is X =R I , R IX =R II , R VIII=R III , R VII =R IV and R V =R VI A synthetic scheme is provided for an organic molecule according to the present invention, which is: [ka]

[0151] Another one-pot procedure to convert I5 to P2 [ka]

[0152] General procedure for synthetic AAV6 [ka]

[0153] E3 (1.00 equivalents), E1 (2.20 equivalents), tris(dibenzylideneacetone)dipalladium Pd2(dba)3 (0.01 equivalents, CAS: 51364-51-3), tri-tert-butylphosphine (P( t Bu)3, CAS: 13716-12-6, 0.04 equivalents) and sodium tert-butoxide (NaO t Bu (3.30 equiv.) was stirred in toluene under a nitrogen atmosphere at 80 °C for 1-16 h. After cooling to room temperature (rt), the reaction mixture was extracted with toluene and water, and the phases were separated. The combined organic layers were dried over MgSO4, and the solvent was removed under reduced pressure. The resulting crude product was purified by recrystallization or column chromatography to give I4 as a solid or oil.

[0154] General procedure for synthetic AAV7 [ka]

[0155] I4 (1.00 equiv.), E2.2 (2.20 equiv.), tris(dibenzylideneacetone)dipalladium Pd2(dba)3 (0.02 equiv., CAS: 51364-51-3), tri-tert-butylphosphine (0.08 equiv., P( t Bu)3, CAS: 13716-12-6) and sodium tert-butoxide (NaO t Bu (3.30 equiv.) was stirred in toluene under a nitrogen atmosphere at 110 °C for 1-16 h. After cooling to room temperature (rt), the reaction mixture was extracted with toluene and water, and the phases were separated. The combined organic layers were dried over MgSO4, and the solvent was removed under reduced pressure. The resulting crude product was purified by recrystallization or column chromatography to give I5 as a solid. [ka]

[0156] Compound I5 was used as the starting material to afford the boronate ester I6 via AAV3. Alternatively, trimethylborate can be used as a boronating reagent to generate the boronic acid derivative corresponding to I6. [ka]

[0157] The target compound P2 is synthesized by AAV4 using the boronic ester I6 as the starting material. Alternatively, the boronic acid corresponding to I6 can be used as the starting material for the synthesis of P2.

[0158] Another one-pot procedure to convert I5 to P2

[0159] [ka]

[0160] The synthesis of target material P2 is achieved via a one-pot protocol, where the chloride precursor I5 is directly converted to P2 by the procedure described in AAV5.

[0161] General Synthesis Method III General synthetic scheme III is a contemplated alternative to schemes I and II (i.e., R X =R I , R IX =R II , R VIII =R III , R VII =R IV and R V =R VI ) is applied to the organic molecules according to the present invention.

[0162] [ka]

[0163] The synthesis of compound I7.1 is carried out by the procedure described in AAV1 using E2.2 (1.1 equivalents) and amine E1 as reactants.

[0164] [ka]

[0165] The synthesis of compound I7.2 is carried out by the procedure described in AAV1 using E2.2 (1.1 equivalents) and amine E1 as reactants.

[0166] [ka]

[0167] Compound I8 is synthesized by AAV8.

[0168] [ka]

[0169] Compound I9 is ​​synthesized by AAV9.

[0170] [ka]

[0171] The synthesis of boronic ester I10 is carried out as described in AAV3 using precursor I9 as substrate. Alternatively, trimethylborate can be used as a boronating reagent to generate the boronic acid derivative corresponding to I10.

[0172] [ka]

[0173] The target compound P3 is synthesized by AAV4 using the boronic ester I10 as the starting material. Alternatively, the boronic acid corresponding to I10 can be used as the starting material for the synthesis of P3.

[0174] Another one-pot procedure to convert I9 to P3

[0175] [ka] The synthesis of target material P3 is achieved via a one-pot protocol, where the chloride precursor I9 is ​​directly converted to P3 by the procedure described in AAV5.

[0176] General procedure for synthetic AAV8

[0177] [ka] E3.2 (1.10 equiv.), I7.1 (1.00 equiv.), tris(dibenzylideneacetone)dipalladium Pd2(dba)3 (0.01 equiv., CAS: 51364-51-3), tri-tert-butylphosphine (P( t Bu)3, CAS: 13716-12-6, 0.04 equivalents) and sodium tert-butoxide (NaO tBu; 1.70 equiv.) in toluene is stirred at 80° C. under a nitrogen atmosphere for 5 h. After cooling to room temperature (rt), the reaction mixture is extracted with toluene and brine, and the phases are separated. The combined organic layers are dried over MgSO4, and the solvent is removed under reduced pressure. The resulting crude product is purified by recrystallization or column chromatography to give I8 as a solid.

[0178] General procedure for synthetic AAV9

[0179] [ka]

[0180] I7.2 (1.10 equiv.), I8 (1.00 equiv.), tris(dibenzylideneacetone)dipalladium Pd2(dba)3 (0.01 equiv., CAS: 51364-51-3), tri-tert-butylphosphine (P( t Bu)3, CAS: 13716-12-6, 0.04 equivalents) and sodium tert-butoxide (NaO t Bu; 1.70 equiv.) in toluene is stirred at 110° C. for 5 h under a nitrogen atmosphere. After cooling to room temperature (rt), the reaction mixture is extracted with toluene and brine, and the phases are separated. The combined organic layers are dried over MgSO4, and the solvent is removed under reduced pressure. The resulting crude product is purified by recrystallization or column chromatography to give I9 ​​as a solid.

[0181] General Synthesis Method IV The general synthesis method IV is R X =R I , R IX =R II , R VIII =R III , R VII =R IV and R V =R VI A synthetic scheme is provided for an organic molecule according to the present invention, which is:

[0182] [ka]

[0183] The synthesis of the dichloro derivative I2-Cl is carried out as described in AAV2 starting from 1,3-dibromo-2,5-dichlorobenzene (1.0 equiv., CAS: 81067-41-6) and the amine I2.

[0184] JPEG0007762670000065.jpg58160

[0185] The boronic ester I3-Cl is synthesized from I2-Cl by the procedure of AAV3, where alternatively, trimethylborate can be used as the boronating reagent to generate the corresponding boronic acid derivative of I3-Cl.

[0186] [ka]

[0187] The parachloro derivative P1-Cl is synthesized from P1-Cl as described in AAV4.

[0188] Alternatively, the boronic acid derivative corresponding to the material I3-Cl can be used as the starting material under the same conditions to generate P1-Cl.

[0189] Another one-pot cyclization method for directly converting I2-Cl to P1-Cl

[0190] [ka] The one-pot synthesis of P1-Cl starting from I2-Cl is carried out as described in AAV5.

[0191] General procedure for synthesizing AAV10

[0192] [ka]

[0193] Under a nitrogen atmosphere, compound P1-Cl (1.0 equivalent) and boronic acid R V -B(OH)2 (6.0 equiv.), palladium-(II)-acetate (0.06 equiv., CAS: 3375-31-3), X-Phos (0.24 equiv., CAS: 564483-18-7), and tripotassium phosphate (9.0 equiv., CAS: 7778-53-2) are stirred in a mixture of toluene and dioxane (1:1) at 100 °C for 1 h. After cooling to room temperature (rt), the reaction mixture is extracted with toluene and water, and the phases are separated. The combined organic layers are treated with activated carbon for 10 min and then filtered through a Celite® (kieselgur) pad. The filtrate is dried over MgSO4, and the solvent is removed under reduced pressure. The resulting crude product is purified by recrystallization or column chromatography to give P1 as a solid.

[0194] General synthesis method V General synthetic scheme V provides a synthetic approach to organic molecules according to the invention, where R X =R I , R IX =R II , R VIII =R III , R VII =R IV and R V =R VI Is:

[0195] [ka]

[0196] Compound I4-Cl was synthesized by procedure AAV6 using 1,3-dibromo-2,5-dichlorobenzene (1.0 equivalent, CAS: 81067-41-6) and primary amine E1 as reactants.

[0197] [ka]

[0198] Compound I5-Cl is obtained by procedure AAV7 using secondary bisamine I4-Cl and 1-bromo-3,5-diphenylbenzene (CAS: 103068-20-8) as reactants.

[0199] [ka]

[0200] The boronic ester I6-Cl can be obtained by AAV3 using compound I5-Cl as the starting material. Alternatively, under the same conditions, trimethylborate can be used as a boronating reagent to generate the corresponding boronic acid derivative of I6-Cl.

[0201] [ka]

[0202] The synthesis of P2-Cl is carried out as described for AAV5 using I5-Cl as substrate.

[0203] [ka]

[0204] The target material P2 is synthesized as described for AAV10 using P2-Cl as the starting material.

[0205] General Synthesis Method VI General Synthetic Scheme VI, Limitations of Schemes I and II (i.e., R X =R I , R IX =R II , R VIII =R III , R VII =R IV and R V =R VI ) is applied to the organic molecules according to the present invention.

[0206] [ka]

[0207] Compound I8-Cl was synthesized as described in AAV8, where 1-bromo-2,3,5-trichlorobenzene (1.0 equivalent) and primary amine I7.1 were used as reactants.

[0208] [ka]

[0209] Compound I9-Cl is synthesized from I7.2 and I8-Cl by AAV9.

[0210] [ka]

[0211] The synthesis of the boronic ester I10-Cl is carried out as described in AAV3 using the precursor I9-Cl as the substrate. Alternatively, trimethylborate can be used as the boronating reagent to generate the boronic acid derivative corresponding to I10-Cl.

[0212] [ka]

[0213] Compound P3-Cl is synthesized by AAV4 using the boronic acid ester I10-Cl as the starting material. Alternatively, the boronic acid corresponding to I10-Cl can be used as the starting material for the synthesis of P3-Cl.

[0214] An alternative one-pot procedure for converting I9-Cl to P3-Cl

[0215] [ka]

[0216] The synthesis of P3-Cl is carried out as described for AAV5 using I9-Cl as substrate.

[0217] [ka]

[0218] The target material P3 is synthesized as described for AAV10 using P3-Cl as the starting material.

[0219] cyclic voltmeter The cyclic voltage and current are measured in dichloromethane, or a suitable solvent, and a suitable supporting electrolyte (e.g., 0.1 mol / L tetrabutylammonium hexafluorophosphate) at a concentration of 10 -3 The measurement was carried out at room temperature in a nitrogen atmosphere using a three-electrode assembly (working electrode and counter electrode: Pt wire, reference electrode: Pt wire) and FeCp2 / FeCp2 as an internal standard. + The HOMO data were corrected using perocene as an internal standard relative to a saturated calomel electrode (SCE).

[0220] Density functional theory calculations The molecular structures were optimized using the BP86 function and the RI (Resolution of Identity) approach. The excitation energies were calculated with the TD-DFT (Time-Dependent DFT) method using the (BP86) optimized structures. The orbital energies and excited-state energies were calculated using the B3LYP function. The Def2-SVP basis set and m4-grid were used for numerical integration. The Turbomole program package was used for all calculations.

[0221] optical physical measurements Sample pretreatment: spin coating Equipment: Spin150, SPS euro The sample concentration is 10 mg / ml dissolved in an appropriate solvent.

[0222] Program: 1) 400 U / min for 3 seconds, 1000 U / min for 20 seconds (1000 U / m / s). 3) 4000 U / min for 10 seconds (1000 U / m / s). After coating, the film was dried at 70°C for 1 minute.

[0223] Photoluminescence spectroscopy and time-correlated single photon coefficient (TCSPC) Steady-state emission spectroscopy was recorded using a Model FluoroMax-4 (Horiba Scientific) equipped with a 150 W xenon-Arc lamp, excitation and emission monochromators, a Hamamatsu R928 photomultiplier tube, and time-correlated single-photon counting options. Standard correction fits were used to correct the emission and excitation spectra. Excited state lifetimes are determined using the same system using the TCSPC method with an FM-2013 instrument and a Horiba Yvon TCSPC hub.

[0224] Excitation light source: NanoLED 370 (wavelength: 371 nm, pulse duration: 1.1 ns) NanoLED 290 (wavelength: 294 nm, pulse duration: <1 ns) SpectraLED 310 (wavelength: 314nm) SpectraLED 355 (wavelength: 355nm) Data analysis (exponential fit) is performed using the software suite DataStation and DAS6 analysis software. The fit is determined using the chi-squared test.

[0225] 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.

[0226] The emission maxima are given in nm, the quantum yields Φ are given in % and the CIE coordinates are given as x,y values.

[0227] PLQY is determined using the following protocol: 1) Quality assurance: Anthracene in ethanol (known concentration) is used as a standard. 2) Excitation wavelength: The absorption maximum of the organic molecule is determined and that wavelength is used to excite the molecule. 3) Measurement The quantum yield is measured on a solution or film sample in a nitrogen atmosphere and is calculated using the following equation:

[0228]

number

[0229] where n 光子 indicates the number of photons, and Int indicates the intensity.

[0230] Fabrication and characterization of optoelectronic devices Optoelectronic devices, particularly OLED devices, containing the organic molecules according to the present invention can also be produced by vacuum deposition. When a layer contains one or more compounds, the weight percentage of one or more compounds is indicated in %. The total weight percentage value is 100%, so if no value is specified, the fraction of the compound is the difference between the specified value and 100%.

[0231] Non-fully optimized OLEDs are characterized by measuring the electroluminescence spectrum using standard methods and the intensity- and current-dependent external quantum efficiency (%) calculated using the light and current detected by a photodiode. 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 at which the measured luminance has decreased to 50% of the initial luminance; similarly, LT80 corresponds to the time at which the measured luminance has decreased to 80% of the initial luminance, and LT95 corresponds to the time at which the measured luminance has decreased to 95% of the initial luminance.

[0232] 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:

[0233]

number

[0234] Here, L0 denotes the initial luminance at the applied current density.

[0235] The value corresponds to the average of several pixels (typically 2-8) and the standard deviation among the pixels is provided.

[0236] HPLC-MS HPLC-MS analysis is performed on an Agilent HPLC (1100 series) equipped with an MS-detector (Thermo LTQ XL).

[0237] The general HPLC method is as follows: A reversed-phase column 4.6 mm x 150 mm and 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 for HPLC. HPLC-MS measurements are performed at room temperature (rt) with a gradient.

[0238] [Table 1]

[0239] [Table 2]

[0240] From the analyte solution at a concentration of 0.5 mg / mL, an injection volume of 5 μL is taken for the measurement. The ionization of the probe is carried out by positive (APCI + ) ionization mode or negative (APCI - ) ionization mode using an APCI (atmospheric pressure chemical ionization) source.

[0241] Example 1 [ka] Example 1 is AAV1 (49% yield), in which 4-chlorodiphenylmethane (CAS 831-81-2) was used as reactant E2 and 4-benzylaniline (CAS 1135-12-2) was used as reactant E1; AAV2 (42% yield), in which 1,3-dibromo-2-chlorobenzene (CAS 19230-27-4) was used as reactant E3, and Synthesized by AAV5 (48% yield). MS (HPLC-MS, APCI, pos. ionization), m / z (residence time): 781.6 (6.16 minutes). The emission maximum of Example 1 (2% by weight in PMMA) is 464 nm, the full width at half maximum (FWHM) is 0.17 eV, the CIE y coordinate is 0.12, and the PLQY is 7.3%. The onset of the emission spectrum is determined at 2.79 eV.

[0242] Example 2 [ka]

[0243] Example 2 is AAV1 (49% yield), in which 4-chlorodiphenylmethane (CAS 831-81-2) was used as reactant E2 and 4-benzylaniline (CAS 1135-12-2) was used as reactant E1; AAV2 (69% yield), in which 4-chloro-3,5-dibromotoluene (CAS 202925-05-1) was used as reactant E3, and Synthesized by AAV5 (13% yield). MS (HPLC-MS, APPI, pos. ionization), m / z (residence time): 795.6 (6.26 minutes).

[0244] The emission maximum of Example 2 (2% by weight in PMMA) is 462 nm, the full width at half maximum (FWHM) is 0.17 eV, the CIE y coordinate is 0.11, and the PLQY is 76%. The onset of the emission spectrum is determined at 2.79 eV.

[0245] Example 3 [ka]

[0246] Example 3 is AAV2 (83% yield), in which 1,3-dibromo-2-chlorobenzene (CAS 19230-27-4) and 4,4'-bis(alpha,alpha-dimethylbenzyl)diphenylamine (CAS 10081-67-1) were used as reactants E3 and I1, respectively; AAV3 (32% yield), where trimethylborate (CAS 121-43-7) was used as the boronation reagent to give the boronic acid derivative corresponding to I3, and Synthesized by AAV4 (23% yield).

[0247] MS (HPLC-MS, APPI, pos. ionization), m / z (residence time): 893.7 (7.66 minutes).

[0248] The emission maximum of Example 3 (2% by weight in PMMA) is 462 nm, the full width at half maximum (FWHM) is 0.16 eV, the CIE y coordinate is 0.10, and the PLQY is 80%. The onset of the emission spectrum is determined at 2.79 eV.

[0249] Example 4 [ka]

[0250] Example 4 is AAV2 (72% yield), in which 4-chloro-3,5-dibromotoluene (CAS 202925-05-1) and 4,4'-bis(alpha,alpha-dimethylbenzyl)diphenylamine (CAS 10081-67-1) were used as reactants E3 and I1, respectively; AAV3 (50% yield), in which trimethylborate (CAS 121-43-7) was used as the boronation reagent and the corresponding dichloride I2-Cl was used as the reactant to give the boronic acid derivative corresponding to I3-Cl, AAV4 (58% yield), and AAV10 (81% yield) was synthesized by reacting the corresponding starting material P1-Cl with methaneboronic acid (CAS: 13061-96-6).

[0251] MS (HPLC-MS), m / z (residence time): 907.80 (7.68 minutes).

[0252] The emission maximum of Example 4 (2% by weight in PMMA) is 461 nm, the full width at half maximum (FWHM) is 0.17 eV, the CIE y coordinate is 0.10, and the PLQY is 81%. The onset of the emission spectrum is determined at 2.81 eV.

[0253] Example D1 Example 1 was tested on an OLED D1 fabricated with the following layer structure:

[0254] [Table 3]

[0255] [ka]

[0256] OLED D1 is 1000cd / m 2 An external quantum efficiency (EQE) of 12.1% was calculated at 1000 kJ / s. The emission maximum is 468 nm with a FWHM of 26 nm at 3.6 V. The CIEy value is 0.12.

[0257] Example D2 Example 2 was tested on an OLED D2 fabricated with the following layer structure:

[0258] [Table 4]

[0259] OLED D2 is 1000cd / m 2 An external quantum efficiency (EQE) of 10.9% was calculated at 1000 V. The emission maximum is 464 nm, with a FWHM of 28 nm at 3.8 V. The CIEy value is 0.10.

[0260] Example D3 Example 3 was tested on an OLED D3 fabricated with the following layer structure:

[0261] [Table 5]

[0262] OLED D3 is 1000cd / m 2 An external quantum efficiency (EQE) of 11.8% was calculated at 1000 V. The emission maximum is 466 nm with a FWHM of 26 nm at 3.5 V. The CIEy value is 0.10.

[0263] Example D4 Example 4 was tested on an OLED D4 fabricated with the following layer structure:

[0264] [Table 6]

[0265] OLED D4 is 1000cd / m 2 An external quantum efficiency (EQE) of 11.2% was calculated at 1000 V. The emission maximum is 464 nm with a FWHM of 26 nm at 3.6 V. The CIEy value is 0.09.

[0266] Additional Examples of Organic Molecules of the Invention [ka]

[0267] [ka]

[0268] [ka]

[0269] [ka]

[0270] [ka]

[0271] [ka]

[0272] [ka]

Claims

1. An organic molecule comprising a structure selected from the group consisting of formula IIIa-1 and formula IIIb-1: 【Chemistry 1】 【Chemistry 2】 wherein n, at each occurrence, is an integer selected from the group consisting of 0, 1, 2, 3, 4, and 5; R6 in each case is hydrogen, deuterium, or C １ -C ５ are independently selected from the group consisting of alkyl, R XI is selected from the group consisting of hydrogen, deuterium, and chlorine.

2. The organic molecule of claim 1, having a structure selected from the group consisting of: Formula IV-1, Formula IV-2, Formula IV-3, and Formula IV-4: 【Transformation 3】 【Chemistry 4】 【Transformation 5】 【Transformation 6】

3. R ＸＩ The organic molecule according to claim 1 or 2, wherein is hydrogen.

4. Use of an organic molecule according to any one of claims 1 to 3 as a light emitter in an optoelectronic device.

5. 5. The use according to claim 4, wherein the optoelectronic element is selected from the group consisting of: ・Organic light-emitting diode (OLED) ・Light-emitting electrochemical cells ・OLED sensor ・Organic diode ・Organic solar cells ・Organic transistor ・Organic field-effect transistor ・Organic laser ・Downward conversion element.

6. A composition comprising: (a) an organic molecule according to any one of claims 1 to 3 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.

7. An optoelectronic device comprising an organic molecule according to any one of claims 1 to 3 or a composition according to claim 6, 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.

8. -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 7 , wherein the light-emitting layer is disposed between the anode and the cathode and comprises the organic molecule or the composition.

9. 10. A method for manufacturing an optoelectronic device, comprising the steps of: processing an organic molecule according to any one of claims 1 to 3 or a composition according to claim 6 by a vacuum evaporation method or from a solution.

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