Organic Molecules for Optoelectronic Devices

Abstract

The invention relates to organic molecules applied in optoelectronic devices. According to the invention, the organic molecule has a structure of formula (I): wherein, both groups T are R 1 or both groups V are R 1 , rather than R 1 The group T or group V selected from the group consisting of: hydrogen; deuterium; R 1 ; C 1 -C 5 alkyl; and Ph (=phenyl), optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu and Ph; R 1 is a methyl group substituted with two groups R 6 and an optionally substituted phenyl group with R 6 : bonded via the positions marked by the dotted line; and, n is an integer selected from the group consisting of 0, 1, 2, 3, 4 and 5.

Description

Technical Field

[0001] The invention relates to organic molecules and to the use of organic molecules in organic light emitting diodes (OLEDs) and in other optoelectronic devices. Background Art

[0002] The use of organic molecules in optoelectronic devices is being actively developed. Summary of the Invention

[0003] The object of the present invention is to provide organic molecules suitable for use in optoelectronic devices.

[0004] This object is achieved by an invention which provides a novel organic molecule.

[0005] According to the invention, the organic molecule is a pure organic molecule, i.e., it does not contain any metal ions as compared to metal complexes known for use in optoelectronic devices. However, the organic molecule of the invention includes a metalloid (specifically, B, Si, Sn, Se, and / or Ge).

[0006] According to the present invention, the organic molecule exhibits an emission maximum in the blue spectral range, sky blue spectral range, or green spectral range. Specifically, the organic molecule exhibits an emission maximum between 420 nm and 520 nm (preferably between 440 nm and 495 nm, more preferably between 450 nm and 470 nm). Specifically, the photoluminescence quantum yield of the organic molecule according to the invention is 50% or greater. The use of the organic molecule according to the invention in an optoelectronic device (e.g., an organic light emitting diode (OLED)) results in a higher efficiency or higher color purity of the optoelectronic device (which is expressed by the full width at half maximum (FWHM) of the emission). The corresponding OLED has higher stability than an OLED having a known emitter material and comparable color.

[0007] The organic molecule according to the invention comprises or consists of the structure of formula I

[0008]

[0009] wherein

[0010] both groups T are R 1 or both groups V are R 1 , rather than R 1 and the group T or the group V selected from the group consisting of: hydrogen; deuterium; C 1 -C 5 alkyl; and Ph, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, and Ph;

[0011] Among them,

[0012] R 1 has a structure of formula F below:

[0013]

[0014] That is, R 1 has a structure with a methyl group substituted with two groups R 6 and a phenyl group optionally substituted with n R 6 , where n is an integer selected from the group consisting of 0, 1, 2, 3, 4, and 5 each time it appears;

[0015] The dotted line in formula F marks the bonding position with the structure shown in formula I;

[0016] R 6 independently of each other, each time it appears, is selected from the group consisting of: hydrogen; deuterium; and C 1 -C 5 alkyl;

[0017] R I 、R II 、R III 、R IV 、R V 、R VI 、R VII 、R VIII 、R IX and R X independently of each other, are 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 ; OSO 2 R 5 ; CF 3 ; CN; halogen; C 1 -C 40 alkyl, optionally substituted with one or more substituents R 5 , and wherein one or more non-adjacent CH 2 groups are optionally replaced by 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, SO 2 NR 5 , O, S or CONR 5 Replace; C 1 -C 40 Alkoxy, optionally substituted with one or more substituents R 5 , and wherein one or more non-adjacent CH 2 The group may be optionally replaced by 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, SO 2 NR 5 , O, S or CONR 5 Replace; C 1 -C 40 Thioalkoxy, optionally substituted with one or more substituents R 5 , and wherein one or more non-adjacent CH 2 The group may be optionally replaced by 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, SO 2 NR 5 , O, S or CONR 5 Replace; C 2 -C 40 Alkenyl, optionally substituted with one or more substituents R 5 , and wherein one or more non-adjacent CH 2 The group may be optionally replaced by 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, SO 2 , NR 5 , O, S or CONR 5 substituted; C 2 -C 40 alkynyl, optionally substituted with one or more substituents R 5 , and wherein one or more non-adjacent CH 2 groups are optionally replaced by 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, SO 2 , NR 5 , O, S or CONR 5 substituted; C 6 -C 60 aryl, optionally substituted with one or more substituents R 5 ; and C 3 -C 57 heteroaryl, optionally substituted with one or more substituents R 5 ;

[0018] R 5 is independently selected from the group consisting of: hydrogen; deuterium; OPh (Ph = phenyl); SPh; CF 3 ; CN; F; Si(C 1 -C 5 alkyl) 3 ; Si(Ph) 3 ; C 1 -C 5 alkyl, wherein optionally one or more hydrogen atoms are independently replaced by deuterium, CN, CF 3 or F; C 1 -C 5 alkoxy, wherein optionally one or more hydrogen atoms are independently replaced by deuterium, CN, CF 3 or F; C 1 -C 5Thioalkoxy, wherein optionally one or more hydrogen atoms are independently of each other replaced by deuterium, CN, CF 3 or F; C 2 -C 5 Alkenyl, wherein optionally one or more hydrogen atoms are independently of each other replaced by deuterium, CN, CF 3 or F; C 2 -C 5 Alkynyl, wherein optionally one or more hydrogen atoms are independently of each other replaced by deuterium, CN, CF 3 or F; C 6 -C 18 Aryl, optionally substituted with one or more C 1 -C 5 alkyl substituents; C 3 -C 17 Heteroaryl, optionally substituted with one or more C 1 -C 5 alkyl substituents; N(C 6 -C 18 aryl) 2 ; N(C 3 -C 17 heteroaryl) 2 ; and N(C 3 -C 17 heteroaryl)(C 6 -C 18 aryl).

[0019] R XI is selected from the group consisting of hydrogen, deuterium, chlorine and C 1 -C 5 alkyl.

[0020] According to the invention, both groups T are R 1 or both groups V are R 1 . It is not possible for all variables T and V in formula I to be R 1 .

[0021] In other words, the organic molecules of the invention comprise a structure selected from the group consisting of formula Ia and formula Ib, or consist of a structure selected from the group consisting of formula Ia and formula Ib:

[0022]

[0023] wherein,

[0024] V # is selected from the group consisting of: hydrogen; deuterium; C 1 -C 5 alkyl; and Ph, optionally substituted with substituents independently selected from Me,i Pr, t one or more substituents from the group consisting of Bu and Ph.

[0025]

[0026] Wherein,

[0027] T # is selected from the group consisting of: hydrogen; deuterium; C 1 -C 5 alkyl; and Ph, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu and Ph.

[0028] According to the invention, R 1 is attached via the position marked by the dotted line shown in Formula F, which means that Formula Ia is equivalently represented by the following structure:

[0029]

[0030] and Formula Ib is equivalently represented by the following structure:

[0031]

[0032] The organic molecule of the invention has at least two groups having the structure of Formula F, but may have at most 12 groups having the structure of Formula F. Specific embodiments of the organic molecule have two or four groups having the structure of Formula F.

[0033] In a preferred embodiment, the organic molecule comprises a structure selected from the group consisting of Formula Ia and Formula Ib, or consists of a structure selected from the group consisting of Formula Ia and Formula Ib, wherein T # and V # are selected from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; and Ph, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu and Ph.

[0034] In a preferred embodiment, T and V are selected from the group consisting of: R 1 ; hydrogen; deuterium; Me; i Pr; t Bu; and Ph, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu and Ph.

[0035] Depending on the value of the integer n, R 1 may have the structure shown below:

[0036] For n = 0:

[0037]

[0038] For n = 1:

[0039]

[0040] For n = 2:

[0041]

[0042] For n = 3:

[0043]

[0044] For n = 4

[0045]

[0046] For n = 5

[0047]

[0048] wherein, R 6 is independently selected from the group consisting of: hydrogen; deuterium; and C 1 -C 5 alkyl, wherein, in certain embodiments, C 1 -C 5 alkyl may be Me, i Pr, t Bu or neopentyl.

[0049] In certain embodiments, R 6 is independently selected from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; and neopentyl.

[0050] In other embodiments, R 6 is independently selected from the group consisting of: hydrogen; and Me.

[0051] In a preferred embodiment, R 1 is, each time it appears, from the group consisting of formula R 1a and formula R 1b :

[0052]

[0053] R 1 Specific examples of R include, for example, the following structures:

[0054]

[0055] In a particularly preferred embodiment, R 1 is selected from the group consisting of formula R 1c and formula R 1d :

[0056]

[0057] In one embodiment, R XI is selected from the group consisting of hydrogen, Me, i Pr, and t Bu.

[0058] In one embodiment, R XI is selected from the group consisting of hydrogen or Me.

[0059] In one embodiment, R XI is hydrogen.

[0060] In one embodiment, R XI is chlorine.

[0061] In one embodiment, R XI is Me.

[0062] 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 each independently selected from the group consisting of: R 1 ; hydrogen; deuterium; halogen; Me; i Pr; t Bu; CN; CF 3 ; SiMe 3 ; SiPh 3 ; Ph, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; pyridyl, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3one or more substituents in the group consisting of and Ph; pyrimidinyl, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; carbazolyl, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; triazinyl, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; and N(Ph) 2 .

[0063] 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; t Bu; CN; CF 3 ; Ph, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; pyridinyl, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; pyrimidinyl, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; carbazolyl, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; triazinyl, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, tOne or more substituents selected from the group consisting of Bu, CN, CF 3 ; and one or more substituents selected from the group consisting of Me, 2 .

[0064] 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 each independently selected from the group consisting of: R 1 ; hydrogen; deuterium; halogen; Me; i Pr; t Bu; CN; CF 3 ; Ph, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; pyridyl, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; pyrimidinyl, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; triazinyl, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; and N(Ph) 2 .

[0065] 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 each independently selected from the group consisting of: R 1 ; hydrogen; deuterium; Me; i Pr; t Bu; Ph, optionally substituted with one or more substituents independently selected from the group consisting of Me,i Pr, t one or more substituents from the group consisting of Bu and Ph; a carbazolyl group, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; and N(Ph) 2 .

[0066] 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; Ph, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu and Ph; and N(Ph) 2 .

[0067] 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; Ph, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu and Ph; and N(Ph) 2 .

[0068] 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 each independently selected from the group consisting of: R 1 ; hydrogen; t Bu; and Ph.

[0069] In one embodiment of the invention, R X = R I , R IX = R II , R VIII = R III , R VII = R IV , and R V = R VI , which results in an organic molecule comprising or consisting of the structure of formula II:

[0070]

[0071] In one embodiment, the organic molecule comprises or consists of the structure of formula II, wherein R I , R II , R III , R IV and R V are each independently selected from the group consisting of: R 1 ; hydrogen; deuterium; halogen; Me; i Pr; t Bu; CN; CF 3 ; SiMe 3 ; SiPh 3 ; Ph, optionally substituted with one or more substituents each independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; pyridyl, optionally substituted with one or more substituents each independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; pyrimidinyl, optionally substituted with one or more substituents each independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; carbazolyl, optionally substituted with one or more substituents each independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; triazinyl, optionally substituted with one or more substituents each independently selected from the group consisting of Me, iPr, t Bu, CN, CF 3 and one or more substituents selected from the group consisting of Ph; and N(Ph) 2 .

[0072] In one embodiment, the organic molecule comprises or consists of Formula II, wherein R I , R II , R III , R IV and R V are independently selected from the group consisting of: R 1 ; hydrogen; deuterium; halogen; Me; i Pr; t Bu; CN; CF 3 ; Ph, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; pyridyl, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; pyrimidinyl, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; carbazolyl, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; triazinyl, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; and N(Ph) 2 .

[0073] In one embodiment, the organic molecule comprises or consists of Formula II, wherein R I , R II , R III , R IV and R V are independently selected from the group consisting of: R 1 ; hydrogen; deuterium; halogen; Me; i Pr; t Bu; CN; CF 3; Ph, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; pyridyl, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; pyrimidinyl, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; triazinyl, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; and N(Ph) 2 .

[0074] In one embodiment, the organic molecule comprises or consists of Formula II, wherein 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; Ph, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu and Ph; carbazolyl, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; and N(Ph) 2 .

[0075] In one embodiment, the organic molecule comprises or consists of Formula II, wherein 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; Ph, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr,t one or more substituents in the group consisting of Bu and Ph; and N(Ph) 2 .

[0076] In one embodiment, the organic molecule comprises or consists of Formula II, wherein R I , R II , R III , R IV and R V are each independently selected from the group consisting of: R 1 ; hydrogen; deuterium; Me; i Pr; t Bu; Ph, optionally substituted with one or more substituents each independently selected from the group consisting of Me, i Pr, t Bu and Ph; and N(Ph) 2 .

[0077] In one embodiment, the organic molecule comprises or consists of Formula II, wherein R I , R II , R III , R IV and R V are each independently selected from the group consisting of: R 1 ; hydrogen; t Bu; and Ph.

[0078] In one embodiment, the organic molecule comprises a structure selected from the group consisting of Formula II-1 and Formula II-2, or consists of a structure selected from the group consisting of Formula II-1 and Formula II-2:

[0079]

[0080] Examples of the organic molecule according to the invention comprising a structure selected from the group consisting of Formula II-1 and Formula II-2, or consisting of a structure selected from the group consisting of Formula II-1 and Formula II-2, are as follows:

[0081]

[0082]

[0083] In a particular embodiment of the invention, the organic molecule comprises a structure selected from the group consisting of Formula IIa, Formula IIb, Formula IIc and Formula IId, or consists of a structure selected from the group consisting of Formula IIa, Formula IIb, Formula IIc and Formula IId:

[0084]

[0085]

[0086] Examples of organic molecules including a structure selected from the group consisting of Formula IIa, Formula IIb, Formula IIc, and Formula IId or consisting of a structure selected from the group consisting of Formula IIa, Formula IIb, Formula IIc, and Formula IId are shown below:

[0087]

[0088] In one embodiment, the organic molecule includes a structure selected from the group consisting of Formula IIIa and Formula IIIb or consists of a structure selected from the group consisting of Formula IIIa and Formula IIIb:

[0089]

[0090] In a preferred embodiment, the organic molecule includes a structure selected from the group consisting of Formula IIIa-1 and Formula IIIb-1 or consists of a structure selected from the group consisting of Formula IIIa-1 and Formula IIIb-1:

[0091]

[0092] In one embodiment, the organic molecule includes a structure selected from the group consisting of Formula IV-1 and Formula IV-2 or consists of a structure selected from the group consisting of Formula IV-1 and Formula IV-2:

[0093]

[0094] In one embodiment, the organic molecule includes a structure selected from the group consisting of Formula IVa and Formula IVb or consists of a structure selected from the group consisting of Formula IVa and Formula IVb:

[0095]

[0096]

[0097] In one embodiment, the organic molecule includes a structure selected from the group consisting of Formula IV-3 and Formula IV-4 or consists of a structure selected from the group consisting of Formula IV-3 and Formula IV-4:

[0098]

[0099] In one embodiment, the organic molecule includes a structure selected from the group consisting of Formula IVc and Formula IVd or consists of a structure selected from the group consisting of Formula IVc and Formula IVd:

[0100] Detailed Description of the Invention

[0101] As used throughout this application, the terms "aryl" and "aromatic" can be understood in the broadest sense to mean any monocyclic, bicyclic or polycyclic aromatic moiety. Thus, aryl contains 6 to 60 aromatic ring atoms and heteroaryl contains 5 to 60 aromatic ring atoms at least one of which is a heteroatom. Nevertheless, throughout the application, the number of aromatic ring atoms may be given as a subscript number in the definition of certain substituents. Specifically, heteroaromatic rings include one to three heteroatoms. Similarly, the terms "heteroaryl" and "heteroaromatic" can be understood in the broadest sense to include any monocyclic, bicyclic or polycyclic heteroaromatic moiety containing at least one heteroatom. The heteroatoms may be the same or different at each occurrence and may be independently selected from the group consisting of N, O, and S. Thus, the term "arylene" refers to a divalent substituent having two points of attachment to other molecular structures and thus serving as a linking group structure. In the case where the groups in the exemplary embodiments are defined differently from the definitions given herein (e.g., the number of aromatic ring atoms or the number of heteroatoms is different from the given definition), the definitions in the exemplary embodiments will apply. According to the invention, fused (cyclized) aromatic polycycles or heteroaromatic polycycles are composed of two or more monocyclic aromatic rings or heteroaromatic rings that form polycycles via a condensation reaction.

[0102] Specifically, as used throughout, the term "aryl or heteroaryl" includes groups that can be attached at any position via an aromatic group or a heteroaromatic group, and the groups are derived from benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, perylene, fluoranthene, benzanthracene, benzophenanthrene, tetracene, pentacene, benzopyrene, 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, naphthimidazole, phenanthrimidazole, pyridineimidazole, pyrazineimidazole, quinoxalineimidazole, 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 combinations of the above groups.

[0103] As used throughout, the term "ring group" can be understood in the broadest sense to mean any monocyclic moiety, bicyclic moiety, or polycyclic moiety.

[0104] As used throughout, the term "biphenyl" as a substituent can be understood in the broadest sense to mean o-biphenyl, m-biphenyl, or p-biphenyl, where ortho, meta, and para are defined with respect to the binding site to another chemical moiety.

[0105] As used throughout, the term "alkyl" can be understood in the broadest sense to mean any straight-chain, branched-chain, or cyclic alkyl substituent. Specifically, the term alkyl includes substituents such as methyl (Me), ethyl (Et), n-propyl ( n Pr), isopropyl ( i Pr), cyclopropyl, n-butyl ( n Bu), isobutyl ( i Bu), sec-butyl ( s Bu), tert-butyl ( t Bu), cyclobutyl, 2-methylbutyl, n-pentyl, sec-pentyl, tert-pentyl, 2-pentyl, neopentyl, cyclopentyl, n-hexyl, sec-hexyl, tert-hexyl, 2-hexyl, 3-hexyl, neohexyl, 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-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-dodec-1-yl, 1,1-diethyl-n-tetradec-1-yl, 1,1-diethyl-n-hexadec-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.

[0106] As used throughout the text, the term "alkenyl" includes straight chain, branched and cyclic alkenyl substituents. The term "alkenyl" for example includes such substituents: vinyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl or cyclooctadienyl.

[0107] As used throughout, the term "alkynyl" includes straight chain, branched and cyclic alkynyl substituents. The term "alkynyl" includes, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl.

[0108] As used throughout, the term "alkoxy" includes linear, branched and cyclic alkoxy substituents. The term "alkoxy" illustratively includes methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy and 2-methylbutoxy.

[0109] As used throughout, the term "thioalkoxy" includes straight chain, branched, and cyclic thioalkoxy substituents wherein the O of the exemplary alkoxy group is replaced with S.

[0110] As used throughout, the terms "halogen" and "halo" may be understood in the broadest sense as preferably fluorine, chlorine, bromine or iodine.

[0111] Whenever hydrogen (H) is mentioned herein, hydrogen (H) may also be replaced by deuterium at each occurrence.

[0112] It will be understood that when a molecular fragment is described as a substituent or otherwise attached to another moiety, its name can be written as if it is a fragment (e.g., naphthyl, dibenzofuranyl) or as if it is the entire molecule (e.g., naphthalene, dibenzofuran). As used herein, these different ways of specifying a substituent or attaching a fragment are considered equivalent.

[0113] In one embodiment, the organic molecules according to the invention have an excited state lifetime of no more than 150 μs, no more than 100 μs, specifically no more than 50 μs, more preferably no more than 10 μs or no more than 7 μs in a film of poly(methyl methacrylate) (PMMA) having 2 wt % of organic molecules at room temperature.

[0114] In yet another embodiment of the invention, the organic molecules according to the invention have an emission peak in the visible light or closest ultraviolet light range (i.e., in the wavelength range of 380 nm to 800 nm) at room temperature and a half-maximum full width 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) in a film of poly(methyl methacrylate) (PMMA) having 2 wt % of the organic molecules.

[0115] The orbital and excited state energies can also be determined by experimental methods. The highest occupied molecular orbital energy (E HOMO ) is determined by cyclic voltammetry with an accuracy of 0.1 eV via methods known to those skilled in the art. The lowest unoccupied molecular orbital energy (E LUMO ) is calculated as E HOMO +E gap , where E gap is determined as follows: for the host compound, unless otherwise stated, the starting point of the emission spectrum of a film with 10 wt% host in poly(methyl methacrylate) (PMMA) is used as E gap . For the emitter molecule, E gap is determined as the energy at which the excitation spectrum and the emission spectrum of a film with 10 wt% emitter in PMMA cross. For the organic molecules according to the invention, E gap is determined as the energy at which the excitation spectrum and the emission spectrum of a film with 2 wt% organic molecules according to the invention in PMMA cross.

[0116] The energy of the first excited triplet state (T1) is determined by the starting point of the emission spectrum at low temperature (usually, at 77 K). For host compounds where the energy difference between the first excited singlet state and the lowest triplet state is > 0.4 eV, phosphorescence is usually visible in the steady-state spectrum in 2-Me-THF. Thus, the triplet energy can be determined as the starting point of the phosphorescence spectrum. For TADF emitter molecules, unless otherwise stated, the energy of the first excited triplet state (T1) is determined by the starting point of the delayed emission spectrum at 77 K, which is measured in a PMMA film with 10 wt% emitter and, in the case of the organic molecules according to the invention, 2 wt% of the organic molecules according to the invention. For both host and emitter compounds, unless otherwise stated, the energy of the first excited singlet state (S1) is determined by the starting point of the emission spectrum, which is measured in a PMMA film with 10 wt% host or emitter compound and, in the case of the organic molecules according to the invention, 2 wt% of the organic molecules according to the invention.

[0117] The starting point of the emission spectrum is determined by calculating the intersection of the tangent of the emission spectrum with the x-axis. The tangent of the emission spectrum is set at the high-energy side of the emission band and at the point of half maximum of the maximum intensity of the emission spectrum.

[0118] In one embodiment, the organic molecule according to the invention has, at room temperature, in a film of poly(methyl methacrylate) (PMMA) having 2 wt% of the organic molecule, an emission spectrum with a starting point that is energetically close to the emission maximum, i.e., the energy difference between the starting point of the emission spectrum and the energy of the emission maximum is lower than 0.14 eV (preferably lower than 0.13 eV, or even lower than 0.12 eV), while the full width at half maximum (FWHM) of the organic molecule 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 less than 0.17 eV), such that the CIEy coordinate is lower than 0.20 (preferably lower than 0.18, more preferably lower than 0.16, or even more preferably lower than 0.14).

[0119] Another aspect of the invention relates to the use of the organic molecule according to the invention as a light-emitting emitter or as an absorber and / or as a host material and / or as an electron transport material and / or as a hole injection material and / or as a hole blocking material in optoelectronic devices.

[0120] A preferred embodiment relates to the use of the organic molecule according to the invention as a light-emitting emitter in optoelectronic devices.

[0121] Optoelectronic devices can be understood in the broadest sense as any device based on organic materials that is suitable for emitting visible light or light in the range closest to ultraviolet (UV) light (i.e., in the wavelength range of 380 nm to 800 nm). More preferably, the optoelectronic device can be capable of emitting light in the visible light range (i.e., 400 nm to 800 nm).

[0122] In the context of such use, optoelectronic devices are more specifically selected from the group consisting of:

[0123] · Organic light-emitting diodes (OLEDs);

[0124] · Light-emitting electrochemical cells;

[0125] · OLED sensors, especially gas and vapor sensors that are not hermetically isolated from the surroundings;

[0126] · Organic diodes;

[0127] · Organic solar cells;

[0128] · Organic transistors;

[0129] · Organic field-effect transistors;

[0130] · Organic lasers; and

[0131] · Down-conversion elements.

[0132] In a preferred embodiment in the context of this application, 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.

[0133] In the case of this application, the fraction of the organic molecules according to the invention in the emission layer in the optoelectronic device (more specifically, in the OLED) is from 0.1% by weight to 99% by weight (more specifically, from 1% by weight to 80% by weight). In an alternative embodiment, the proportion of the organic molecules in the emission layer is 100% by weight.

[0134] In one embodiment, the light-emitting layer (or "emission layer") includes not only the organic molecules according to the invention, but also a host material whose triplet (T1) energy level and singlet (S1) energy level are higher in energy than the triplet (T1) energy level and singlet (S1) energy level of the organic molecules.

[0135] Another aspect of the invention relates to a composition that comprises or consists of the following components:

[0136] (a) at least one organic molecule according to the invention, specifically in the form of an emitter and / or a host; and

[0137] (b) one or more emitter and / or host materials different from the organic molecules according to the invention; and

[0138] (c) optionally, one or more dyes and / or one or more solvents.

[0139] In one embodiment, the light-emitting layer comprises (or consists essentially of) a composition that comprises or consists of the following components:

[0140] (a) at least one organic molecule according to the invention, specifically in the form of an emitter and / or a host; and

[0141] (b) one or more emitter and / or host materials different from the organic molecules according to the invention; and

[0142] (c) optionally, one or more dyes and / or one or more solvents.

[0143] In a specific embodiment, the light-emitting layer (EML) comprises (or consists essentially of) a composition that comprises or consists of the following components:

[0144] (i) from 0.1% by weight to 10% by weight (preferably, from 0.5% by weight to 5% by weight, specifically from 1% by weight to 3% by weight) of one or more organic molecules (E) according to the invention;

[0145] (ii) from 5% to 99% by weight (preferably from 15% to 85% by weight, specifically from 20% to 75% by weight) of at least one host compound (H); and

[0146] (iii) from 0.9% to 94.9% by weight (preferably from 14.5% to 80% by weight, specifically from 24% to 77% by weight) of at least one other host compound (D), which other host compound (D) has a structure different from the structure of the organic molecule according to the invention; and

[0147] (iv) optionally, from 0% to 94% by weight (preferably from 0% to 65% by weight, specifically from 0% to 50% by weight) of a solvent; and

[0148] (v) optionally, from 0% to 30% by weight (specifically from 0% to 20% by weight, preferably from 0% to 5% by weight) of at least one other emitter molecule (F), which other emitter molecule (F) has a structure different from the structure of the organic molecule according to the invention.

[0149] Preferably, energy can be transferred from the host compound (H) to one or more organic molecules according to the invention. Specifically, energy can be transferred 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.

[0150] In one embodiment, the host compound (H) has a highest occupied molecular orbital (HOMO(H)) having an energy (E HOMO (H)) in the range of -5 eV to -6.5 eV, and at least one other host compound (D) has a highest occupied molecular orbital (HOMO(D)) having an energy (E HOMO (D)), wherein E HOMO (H)>E HOMO (D).

[0151] In another embodiment, the host compound (H) has a lowest unoccupied molecular orbital (LUMO(H)) having an energy (E LUMO (H)), and at least one other host compound (D) has a lowest unoccupied molecular orbital (LUMO(D)) having an energy (E LUMO (D)), wherein E LUMO (H)>E LUMO (D).

[0152] In one embodiment, the host compound (H) has a highest occupied molecular orbital (HOMO(H)) having an energy (E HOMO (H)) and a lowest unoccupied molecular orbital (LUMO(H)) having an energy (E LUMO (H)), and

[0153] at least one other host compound (D) has a highest occupied molecular orbital (HOMO(D)) having an energy (E HOMO (D)) and a lowest unoccupied molecular orbital (LUMO(D)) having an energy (E LUMO (D)),

[0154] The organic molecule (E) according to the invention has a highest occupied molecular orbital (HOMO(E)) having an energy (E HOMO (E)) and a lowest unoccupied molecular orbital (LUMO(E)) having an energy (E LUMO (E)),

[0155] wherein,

[0156] E HOMO (H)>E HOMO (D), and the difference between the energy level (E HOMO (E)) of the highest occupied molecular orbital (HOMO(E)) of the organic molecule (E) according to the invention and the energy level (E HOMO (H)) of the highest occupied molecular orbital (HOMO(H)) of the host compound (H) is between -0.5 eV and 0.5 eV (more preferably between -0.3 eV and 0.3 eV, even more preferably between -0.2 eV and 0.2 eV, or even between -0.1 eV and 0.1 eV); and

[0157] E LUMO (H)>E LUMO (D), and the difference between the energy level (E LUMO (E)) of the lowest unoccupied molecular orbital (LUMO(E)) of the organic molecule (E) according to the invention and the energy level (E LUMO (D)) of the lowest unoccupied molecular orbital (LUMO(D)) of at least one other host compound D is between -0.5 eV and 0.5 eV (more preferably between -0.3 eV and 0.3 eV, even more preferably between -0.2 eV and 0.2 eV, or even between -0.1 eV and 0.1 eV).

[0158] In one embodiment of the invention, the host compound (D) and / or the host compound (H) is a thermally activated delayed fluorescence (TADF) material. The TADF material exhibits a same less than 2500 cm -1The energy difference between the first excited singlet state (S1) and the first excited triplet state (T1) corresponds to ΔE ST Preferably, the TADF material exhibits a -1 , more preferably less than 1500cm -1 , even more preferably less than 1000 cm -1 Or even less than 500cm -1 ΔE ST value.

[0159] In one embodiment, the host compound (D) is a TADF material, and the host compound (H) exhibits a relative humidity greater than 2500 cm -1 ΔE ST In a specific embodiment, the host compound (D) is a TADF material, and the host compound (H) is selected from the group consisting of CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophene-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole and 9-[3,5-bis(2-dibenzothiophene)phenyl]-9H-carbazole.

[0160] In one embodiment, the host compound (H) is a TADF material and the host compound (D) exhibits a relative humidity greater than 2500 cm -1 ΔE ST In a specific embodiment, the host compound (H) is a TADF material, and the host compound (D) is selected from the group consisting of T2T (2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine), T3T (2,4,6-tris(terphenyl-3-yl)-1,3,5-triazine) and / or TST (2,4,6-tris(9,9'-spirobifluorene-2-yl)-1,3,5-triazine).

[0161] In yet another aspect, the invention relates to an optoelectronic device comprising an organic molecule as described herein or a composition of the type described herein, the optoelectronic device more particularly being in 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 (more particularly, a gas and vapor sensor that is not sealed externally isolated), an organic diode, an organic solar cell, an organic transistor, an organic field effect transistor, an organic laser, and a down-conversion element.

[0162] 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.

[0163] In one embodiment of the optoelectronic device of the invention, the organic molecule (E) according to the invention is used as the emissive material in the emissive layer (EML).

[0164] In one embodiment of the optoelectronic device of the invention, the emissive layer (EML) consists of the composition according to the invention described herein.

[0165] When the optoelectronic device is an OLED, it may have, for example, the following layer structure:

[0166] 1. Substrate

[0167] 2. Anode layer, A

[0168] 3. Hole injection layer, HIL

[0169] 4. Hole transport layer, HTL

[0170] 5. Electron blocking layer, EBL

[0171] 6. Emissive layer, EML

[0172] 7. Hole blocking layer, HBL

[0173] 8. Electron transport layer, ETL

[0174] 9. Electron injection layer, EIL

[0175] 10. Cathode layer, C

[0176] Wherein, the OLED includes each layer selected from the group consisting of HIL, HTL, EBL, HBL, ETL, and EIL. Optionally only, different layers may be combined, and the OLED may include more than one layer of each layer type defined above.

[0177] In addition, in one embodiment, the optoelectronic device may include one or more protective layers that protect the device from damage caused by exposure to harmful substances in the environment (including, for example, moisture, vapor, and / or gas).

[0178] In one embodiment of the invention, the optoelectronic device is an OLED having the following inverted layer structure:

[0179] 1. Substrate

[0180] 2. Cathode layer, C

[0181] 3. Electron injection layer, EIL

[0182] 4. Electron transport layer, ETL

[0183] 5. Hole blocking layer, HBL

[0184] 6. Emissive layer, EML

[0185] 7. Electron blocking layer, EBL

[0186] 8. Hole transport layer, HTL

[0187] 9. Hole injection layer, HIL

[0188] 10. Anode layer, A

[0189] Wherein, the OLED includes each layer selected from the group consisting of HIL, HTL, EBL, HBL, ETL, and EIL. Optionally only, different layers may be combined, and the OLED may include more than one layer of each layer type defined above.

[0190] In one embodiment of the invention, the optoelectronic device is an OLED that can have a stacked architecture. In such an architecture, contrary to a typical arrangement in which OLEDs are placed side by side, the individual units are stacked on top of each other. Hybrid light can be generated with an OLED exhibiting a stacked architecture. Specifically, white light can be generated by stacking a blue OLED, a green OLED, and a red OLED. In addition, an OLED exhibiting a stacked architecture may include a charge generation layer (CGL), which is typically positioned between two OLED sub-units and typically consists of an n-doped layer and a p-doped layer, and the n-doped layer of one CGL is typically positioned close to the anode layer.

[0191] In one embodiment of the invention, the optoelectronic device is an OLED that includes two or more emission layers between the anode and the cathode. Specifically, such a so-called tandem OLED includes three emission layers, wherein one emission layer emits red light, one emission layer emits green light, and one emission layer emits blue light, and optionally may further include layers such as charge generation layers, blocking layers, or transport layers between the respective emission layers. In yet another embodiment, the emission layers are stacked adjacent to each other. In yet another embodiment, the tandem OLED includes a charge generation layer between every two emission layers. Additionally, adjacent emission layers or emission layers separated by charge generation layers may be combined.

[0192] The substrate can be formed from any material or combination of materials. Most commonly, a glass slide is used as the substrate. Optionally, a thin metal layer (e.g., a copper, gold, silver, or aluminum film) or a plastic film or glass slide can be used. This can allow a higher degree of flexibility. The anode layer (A) mainly consists of materials that allow for the obtaining of a (substantially) transparent film. Since at least one of the two electrodes should be (substantially) transparent to allow light emission from the OLED, either the anode layer (A) or the cathode layer (C) is transparent. Preferably, the anode layer (A) includes a large amount of transparent conductive oxide (TCO), or even consists of transparent conductive oxide (TCO). Such an anode layer (A) can 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.

[0193] The anode layer (A) can (substantially) consist of indium tin oxide (ITO) (e.g., (InO 3 ) 0.9 (SnO 2 ) 0.1 ). The roughness of the anode layer (A) caused by the transparent conductive oxide (TCO) can be compensated for by using a hole injection layer (HIL). In addition, since the transport of quasi-charge carriers from the TCO to the hole transport layer (HTL) is promoted, the HIL can facilitate the injection of quasi-charge carriers (i.e., holes). The hole injection layer (HIL) can include poly(3,4-ethylenedioxythiophene) (PEDOT), polystyrene sulfonate (PSS), MoO 2 , V 2 O 5, CuPC or CuI (specifically, a mixture of PEDOT and PSS). The hole injection layer (HIL) can also prevent the diffusion of metal from the anode layer (A) into the hole transport layer (HTL). The HIL can include, for example, PEDOT:PSS (poly(3,4-ethylenedioxythiophene):polystyrene sulfonate), PEDOT (poly(3,4-ethylenedioxythiophene)), mMTDATA (4,4',4”-tris[phenyl(m-tolyl)amino]triphenylamine), spiro-TAD (2,2',7,7'-tetrakis(n,n-diphenylamino)-9,9'-spirobifluorene), DNTPD (N1,N1'-(biphenyl-4,4'-diyl)bis(N1-phenyl-N4,N4-di-m-tolylbenzene-1,4-diamine)), NPB (N,N'-bis(1-naphthyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine), NPNPB (N,N'-diphenyl-N,N'-bis[4-(N,N-diphenyl-amino)phenyl]benzidine), MeO-TPD (N,N,N',N'-tetrakis(4-methoxyphenyl)benzidine), HAT-CN (1,4,5,8,9,12-hexaazatriphenylenehexacarbonitrile) and / or spiro-NPD (N,N'-diphenyl-N,N'-bis(1-naphthyl)-9,9'-spirobifluorene-2,7-diamine).

[0194] Adjacent to the anode layer (A) or the hole injection layer (HIL), a hole transport layer (HTL) is typically positioned. 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 emitting layer (EML). The hole transport layer (HTL) can also be an electron blocking layer (EBL). Preferably, the hole transport compound has a relatively high energy level of its triplet state (T1). For example, the hole transport layer (HTL) can include star-shaped heterocycles such as tris(4-carbazol-9-ylphenyl)amine (TCTA), poly-TPD (poly(4-butylphenyl-diphenyl-amine)), α-NPD (2,2'-dimethyl-N,N'-bis[(1-naphthyl)-N,N'-diphenyl]-1,1'-biphenyl-4,4'-diamine), TAPC (4,4'-cyclohexyl-bis[N,N-bis(4-methylphenyl)aniline]), 2-TNATA (4,4',4”-tris[2-naphthyl(phenyl)amino]triphenylamine), spiro-TAD, DNTPD, NPB, NPNPB, MeO-TPD, HAT-CN, and / or Tris-Pcz (9,9'-diphenyl-6-(9-phenyl-9H-carbazol-3-yl)-9H,9'H-3,3'-bicarbazole). Additionally, the HTL can include a p-doped layer that can be composed of an inorganic dopant or an organic dopant in an organic hole transport matrix. Transition metal oxides such as vanadium oxide, molybdenum oxide, or tungsten oxide can be used, for example, as inorganic dopants. Tetrafluoro-tetracyanoquinodimethane (F 4 -TCNQ), copper(I) pentafluorobenzoate (Cu(I)pFBz), or transition metal complexes can be used, for example, as organic dopants.

[0195] The EBL can include, for example, mCP (1,3-bis(carbazol-9-yl)benzene), TCTA, 2-TNATA, mCBP (3,3-bis(9H-carbazol-9-yl)biphenyl), Tris-Pcz, CzSi (9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole), and / or DCB (N,N'-dicarbazolyl-1,4-dimethylbenzene).

[0196] Adjacent to the hole transport layer (HTL), a light emitting layer (EML) is typically positioned. The light emitting layer (EML) includes at least one organic molecule. Specifically, the EML includes at least one organic molecule (E) according to the invention. In one embodiment, the light emitting layer consists only of the organic molecule according to the invention. Typically, the EML additionally includes one or more host materials (H). For example, the host material (H) is selected from CBP (4,4'-bis(N-carbazolyl)biphenyl), mCP, mCBP, Sif87 (dibenzothiophen-2-yltriphenylsilane), CzSi, Sif88 (dibenzothiophen-2-yldiphenylsilane), DPEPO (bis[2-(diphenylphosphino)phenyl]ether oxide), 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, 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole, T2T (2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine), T3T (2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine) and / or TST (2,4,6-tris(9,9'-spirobifluorene-2-yl)-1,3,5-triazine). The host material (H) should typically be selected to exhibit a first triplet (T1) and a first singlet (S1) energy level that is higher in energy than the first triplet (T1) and first singlet (S1) energy levels of the organic molecule.

[0197] In one embodiment of the invention, the EML comprises a so-called hybrid host system having at least one hole-dominant host and one electron-dominant host. In a specific embodiment, the EML exactly comprises an organic molecule according to the invention and a hybrid host system, the hybrid host system comprising T2T as the electron-dominant host and a host selected from 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 as the hole-dominant host. In yet another embodiment, the EML comprises 50 wt% to 80 wt% (preferably 60 wt% to 75 wt%) of a host, 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 the organic molecule according to the invention, the host being selected from 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.

[0198] Adjacent to the emitting layer (EML), an electron transport layer (ETL) can be positioned. Here, any electron transport agent can be used. Exemplarily, electron-deficient compounds such as benzimidazole, pyridine, triazole, oxadiazole (e.g., 1,3,4-oxadiazole), phosphine oxide and sulfone can be used. The electron transport body can also be a star-shaped heterocycle such as 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi). The ETL can comprise NBphen (2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline), Alq 3 (aluminum tris(8-hydroxyquinoline)), TSPO1 (diphenyl-4-triphenylsilylphenyl-phosphine oxide), BPyTP2 (2,7-bis(2,2'-bipyridin-5-yl)triphenylene), Sif87 (dibenzothiophen-2-yltriphenylsilane), Sif88 (dibenzothiophen-2-yldiphenylsilane), BmPyPhB (1,3-bis[3,5-bis(pyridin-3-yl)phenyl]benzene) and / or BTB (4,4'-bis[2-(4,6-diphenyl-1,3,5-triazinyl)]-1,1'-biphenyl). Optionally, the ETL can 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.

[0199] The HBL may include, for example, BCP (2,9 - dimethyl - 4,7 - diphenyl - 1,10 - phenanthroline = bathocuproine), BAlq (bis(8 - hydroxy - 2 - methylquinolinato)-(4 - phenylphenoxy)aluminum), NBphen (2,9 - bis(naphthalen - 2 - yl)-4,7 - diphenyl - 1,10 - phenanthroline), Alq 3 (tris(8 - hydroxyquinolinato)aluminum), TSPO1 (diphenyl - 4 - triphenylsilylphenyl - phosphine oxide), T2T (2,4,6 - tris(biphenyl - 3 - yl)-1,3,5 - triazine), T3T (2,4,6 - tris(triphenyl - 3 - yl)-1,3,5 - triazine), TST (2,4,6 - tris(9,9'-spirobifluorene - 2 - yl)-1,3,5 - triazine) and / or TCB / TCP (1,3,5 - tris(N - carbazolyl)benzene / 1,3,5 - tris(carbazol - 9 - yl)benzene).

[0200] Adjacent to the electron transport layer (ETL), a cathode layer (C) may be positioned. The cathode layer (C) may include, for example, a metal (such as Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, Li, Ca, Ba, Mg, In, W or Pd) or a metal alloy, or may be composed of a metal (such as Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, Li, Ca, Ba, Mg, In, W or Pd) or a metal alloy. For practical reasons, the cathode layer may also be composed of a (substantially) opaque metal such as Mg, Ca or Al. Optionally or additionally, the cathode layer (C) may also include graphite and / or carbon nanotubes (CNT). Optionally, the cathode layer (C) may also be composed of nanoscale silver wires.

[0201] The OLED may further optionally include a protective layer (which may be designated as an electron injection layer (EIL)) between the electron transport layer (ETL) and the cathode layer (C). This layer may include lithium fluoride, cesium fluoride, silver, Liq (lithium 8 - hydroxyquinolate), Li 2 O, BaF 2 , MgO and / or NaF.

[0202] Optionally, the electron transport layer (ETL) and / or the hole - blocking layer (HBL) may also include one or more host compounds (H).

[0203] To further modify the emission spectrum and / or absorption spectrum of the emissive layer (EML), the emissive layer (EML) may further comprise one or more other emitter molecules (F). Such emitter molecules (F) can be any emitter molecules known in the art. Preferably, such emitter molecules (F) are molecules having a structure different from the structure of the organic molecule (E) according to the invention. The emitter molecule (F) can optionally be a TADF emitter. Optionally, the emitter molecule (F) can optionally be a fluorescent and / or phosphorescent emitter molecule capable of shifting the emission spectrum and / or absorption spectrum of the emissive layer (EML). Exemplarily, by emitting light that is typically redshifted compared to the light emitted by the organic molecule, triplet and / or singlet excitons can be transferred from the organic molecule according to the invention to the emitter molecule (F) before relaxing to the ground state (S0). Optionally, the emitter molecule (F) can also cause a two-photon effect (i.e., absorption of half of the energy of the absorption maximum by two photons).

[0204] Optionally, an optoelectronic device (e.g., an OLED) can be, for example, a substantially white optoelectronic device. For example, such a white optoelectronic device can comprise at least one (deep) blue emitter molecule and one or more emitter molecules that emit green light and / or red light. Then, energy transmittance can also optionally exist between two or more molecules as described above.

[0205] As used herein, if not more specifically defined in a particular context, the designation of the color of emitted and / or absorbed light is as follows:

[0206] Violet: wavelength range of >380 nm to 420 nm;

[0207] Dark blue: wavelength range of >420 nm to 480 nm;

[0208] Sky blue: wavelength range of >480 nm to 500 nm;

[0209] Green: wavelength range of >500 nm to 560 nm;

[0210] Yellow: wavelength range of >560 nm to 580 nm;

[0211] Orange: wavelength range of >580 nm to 620 nm;

[0212] Red: wavelength range of >620 nm to 800 nm.

[0213] For emitter molecules, this color refers to the emission maximum. Thus, for example, a dark blue emitter has an emission maximum in the range of >420 nm to 480 nm, a sky blue emitter has an emission maximum in the range of >480 nm to 500 nm, a green emitter has an emission maximum in the range of >500 nm to 560 nm, and a red emitter has an emission maximum in the range of >620 nm to 800 nm.

[0214] The dark blue emitter may preferably have an emission maximum below 480 nm, more preferably below 470 nm, even more preferably below 465 nm or even below 460 nm. It will typically be above 420 nm, preferably above 430 nm, more preferably above 440 nm or even above 450 nm.

[0215] Thus, yet another aspect of the present invention relates to an OLED that exhibits an external quantum efficiency greater than 8% (more preferably greater than 10%, more preferably greater than 13%, even more preferably greater than 15%, or even greater than 20%) at 1000 cd / m 2 and / or exhibits an emission maximum between 420 nm and 500 nm (preferably between 430 nm and 490 nm, more preferably between 440 nm and 480 nm, even more preferably between 450 nm and 470 nm), and / or exhibits an LT80 value greater than 100 hours (preferably greater than 200 hours, more preferably greater than 400 hours, even more preferably greater than 750 hours, or even greater than 1000 hours) at 500 cd / m 2 Thus, yet another aspect of the present invention relates to an OLED whose emission exhibits a CIEy color coordinate less than 0.45 (preferably less than 0.30, more preferably less than 0.20, or even more preferably less than 0.15, or even less than 0.10).

[0216] Yet another aspect of the present invention relates to an OLED that emits light at different color points. According to the present invention, the OLED emits light having a narrow emission band (small full width at half maximum (FWHM)). In one aspect, the OLED according to the invention emits light having an FWHM of the main emission peak 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 less than 0.17 eV).

[0217] Another aspect of the present invention relates to an OLED that emits light having CIEx and CIEy color coordinates (CIEx = 0.131, CIEy = 0.046), which are close to the CIEx (= 0.131) and CIEy (= 0.046) color coordinates of the primary color blue as defined by ITU-R Recommendation BT.2020 (Rec.2020), and is thus suitable for use in ultra-high definition (UHD) displays (e.g., UHD-TV). Accordingly, another aspect of the present invention relates to an OLED, the emission of which exhibits a CIEx color coordinate between 0.02 and 0.30 (preferably between 0.03 and 0.25, more preferably between 0.05 and 0.20, or even more preferably between 0.08 and 0.18, or even between 0.10 and 0.15) and / or a CIEy color coordinate between 0.00 and 0.45 (preferably between 0.01 and 0.30, more preferably between 0.02 and 0.20, or even more preferably between 0.03 and 0.15, or even between 0.04 and 0.10).

[0218] In yet another aspect, the invention relates to a method for manufacturing an optoelectronic component. In this case, the organic molecules of the invention are used.

[0219] The optoelectronic device (specifically, OLED) according to the present invention can be manufactured by any means of vapor deposition and / or liquid processing. Accordingly, at least one layer:

[0220] - is prepared by a sublimation process,

[0221] - is prepared by an organic vapor deposition process,

[0222] - is prepared by a carrier gas sublimation process,

[0223] - is solution processed or printed.

[0224] The method for manufacturing an optoelectronic device (specifically, OLED) according to the present invention is known in the art. By means of subsequent deposition processes, different layers are deposited individually and successively on a suitable substrate. The same or different deposition methods can be used to deposit the respective layers.

[0225] Vapor deposition processes include, for example, thermal (co)evaporation, chemical vapor deposition, and physical vapor deposition. For active matrix OLED displays, an AMOLED backplane is used as a substrate. The individual layers may be processed from a solution or dispersion using an appropriate solvent. Solution deposition processes include, for example, spin coating, dip coating, and jet printing. Liquid processing may optionally be performed in an inert atmosphere (e.g., in a nitrogen atmosphere), and the solvent may be completely or partially removed by means known in the art.

[0226] Example

[0227] General Synthesis Scheme I

[0228] General Synthetic Scheme I provides a synthetic scheme for organic molecules according to the invention, wherein R X =R I , R IX =R II , R VIII =R III , R VII =R IV , and R V =R VI :

[0229]

[0230]

[0231] Alternatively, trimethyl borate can be used as the borylation reagent to give the corresponding boronic acid derivative of I3.

[0232]

[0233] Alternatively, the corresponding boronic acid derivative of substrate I3 can be used as starting material under the same conditions.Alternative one-pot ring closure scheme for the direct conversion of I2 to P1.

[0234]

[0235] General steps for synthesizing AAV1:

[0236]

[0237] E1 (1.00 equiv.), E2 (1.10 equiv.), tris(dibenzylideneacetone)dipalladium (Pd) were stirred in toluene at 80°C under nitrogen atmosphere. 2 (dba) 3 (0.01 equivalent; CAS: 51364-51-3), tri-tert-butylphosphine (P( t Bu) 3, CAS: 13716-12-6, 0.04 equiv) and sodium tert-butoxide (NaO t Bu; 1.70 equiv) for 1 to 16 hours. After cooling to room temperature (rt), the reaction mixture was extracted with toluene and water, and the phases were separated. 4 The combined organic layers are dried, and then the solvent is removed under reduced pressure. The obtained crude product is purified by recrystallization or column chromatography to obtain I1 as a solid or oil.

[0238] General steps for synthesizing AAV2:

[0239]

[0240] I1 (2.20 equiv.), E3 (1.00 equiv.), tris(dibenzylideneacetone)dipalladium (Pd) were stirred in toluene at 110° C. under a nitrogen atmosphere. 2 (dba) 3 (0.02 equivalent; CAS: 51364-51-3), tri-tert-butylphosphine (0.08 equivalent, P( t Bu) 3 , CAS: 13716-12-6) and sodium tert-butoxide (NaO t Bu; 3.30 equiv) for 1 to 16 hours. After cooling to room temperature (rt), the reaction mixture was extracted with toluene and water, and the phases were separated. 4 The combined organic layers are dried and the solvent is then removed under reduced pressure. The crude product obtained is purified by recrystallization or column chromatography to obtain I2 as a solid.

[0241] General steps for synthesizing AAV3:

[0242]

[0243] Under nitrogen atmosphere, I2 (1.00 equiv.) was dissolved in anhydrous THF. The resulting solution was cooled to -10 °C. Subsequently, tert-BuLi (2.20 equiv., CAS: 594-19-4) was slowly added and stirring was continued at 0 °C. After complete lithiation, 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3.00 equiv., CAS: 61676-62-8, or alternatively, trimethyl borate, CAS121-43-7) was added and then heated at 40 °C for 2 hours. After cooling to room temperature (rt), water was added and the phases were separated. The reaction mixture was washed with anhydrous MgSO 4 The combined organic layers were dried, filtered and concentrated under reduced pressure. The crude product obtained was purified by recrystallization or column chromatography to give I3 or the corresponding boronic acid as a solid, respectively.

[0244] General steps for synthesizing AAV4:

[0245]

[0246] I3 (1.00 equiv.), N,N-diisopropylethylamine (10 equiv., CAS: 7087-68-5) and AlCl were stirred in chlorobenzene at 120 °C under nitrogen atmosphere. 3 (10 equiv., CAS: 7446-70-0) for 4 h. After cooling to room temperature (rt), the reaction mixture was extracted between toluene and water and the phases were separated. 4 The combined organic layers were dried and the solvent was then removed under reduced pressure. The crude product obtained was purified by recrystallization or column chromatography to obtain P1 as a solid.

[0247] General steps for synthesizing AAV5:

[0248]

[0249] I2 (1.00 equiv.) was dissolved in tert-butylbenzene under nitrogen atmosphere, and the solution was cooled to -30°C. tert-butyllithium ( t BuLi) (2.20 equiv., CAS: 594-19-4) solution and the reaction mixture was allowed to warm to 0°C. After stirring at 60°C for 120 min, the t The solvent and by-products of the BuLi solution were removed, and the reaction mixture was cooled to -30°C again. Boron tribromide (BBr 3 , CAS: 10294-33-4, 2.20 equivalents), the cooling bath was removed and the reaction mixture was allowed to warm to room temperature (rt). After stirring at rt for 30 minutes, the reaction mixture was cooled to 0 ° C and N, N-diisopropylethylamine (CAS: 7087-68-5, 3.00 equivalents) was added. The reaction mixture was warmed to rt and then refluxed at 120 ° C for 3 hours. Subsequently, the reaction mixture was poured into water, and the resulting precipitate was filtered and washed with a minimum amount of ethyl acetate to obtain P1 as a solid product. P1 can be further purified by recrystallization or by flash chromatography.

[0250] General Synthetic Scheme II

[0251] General Synthetic Scheme II provides a synthetic scheme for organic molecules according to the invention, wherein R X =R I , R IX =R II , R VIII =R III , R VII =R IV, and R V =R VI :

[0252]

[0253]

[0254] An alternative one-pot procedure for the conversion of I5 to P2.

[0255]

[0256] General steps for synthesizing AAV6

[0257]

[0258] E3 (1.00 equiv.), E1 (2.20 equiv.), tris(dibenzylideneacetone)dipalladium (Pd) were stirred in toluene at 80°C under nitrogen atmosphere. 2 (dba) 3 (0.01 equivalent; CAS: 51364-51-3), tri-tert-butylphosphine (P( t Bu) 3 , CAS: 13716-12-6, 0.04 equiv) and sodium tert-butoxide (NaO t Bu; 3.30 equiv) for 1 to 16 hours. After cooling to room temperature (rt), the reaction mixture was extracted with toluene and water, and the phases were separated. 4 The combined organic layers are dried and the solvent is then removed under reduced pressure. The crude product obtained is purified by recrystallization or column chromatography to obtain I4 as a solid or oil.

[0259] General steps for synthesizing AAV7

[0260]

[0261] I4 (1.00 equiv.), E2.2 (2.20 equiv.), tris(dibenzylideneacetone)dipalladium (Pd) were stirred in toluene at 110°C under nitrogen atmosphere. 2 (dba) 3 (0.02 equivalent; CAS: 51364-51-3), tri-tert-butylphosphine (0.08 equivalent, P( t Bu) 3 , CAS: 13716-12-6) and sodium tert-butoxide (NaO t Bu; 3.30 equiv) for 1 to 16 hours. After cooling to room temperature (rt), the reaction mixture was extracted with toluene and water, and the phases were separated. 4Dry the combined organic layers and then remove the solvent under reduced pressure. Purify the obtained crude product by recrystallization or column chromatography to obtain I5 as a solid.

[0262]

[0263] Obtain borate I6 using compound I5 as a starting material according to AAV3. Optionally, trimethyl borate can be used as the boronating reagent to obtain the corresponding boric acid derivative of I6.

[0264]

[0265] Synthesize the target compound P2 using borate I6 as a starting material according to AAV4. Optionally, the boric acid corresponding to I6 can be used as the starting material for the synthesis of P2.

[0266] An alternative one-pot procedure for converting I5 to P2.

[0267]

[0268] Perform the synthesis of target P2 via a one-pot method, in which the chloride precursor I5 is directly converted to P2 according to the procedure described in AAV5.

[0269] General Synthesis Scheme III

[0270] General Synthesis Scheme III provides a synthesis scheme for organic molecules according to the invention, where the limitations of Scheme I and Scheme II do not apply (i.e., R X = R I , R IX = R II , R VIII = R III , R VII = R IV , and R V = R VI ).

[0271]

[0272] Synthesize compound I7.1 using E2.2 (1.1 equivalents) and amine E1 as reactants according to the procedure described in AAV1.

[0273]

[0274] Synthesize compound I7.2 using E2.2 (1.1 equivalents) and amine E1 as reactants according to the procedure described in AAV1.

[0275]

[0276] Compound I8 was synthesized based on AAV8.

[0277]

[0278] Compound I9 was synthesized based on AAV9.

[0279]

[0280] The synthesis of boronate ester I10 was performed as described in AAV3 using precursor I9 as substrate. Alternatively, trimethyl borate can be used as the borylation reagent to give the corresponding boronic acid derivative of I10.

[0281]

[0282] The target compound P3 was synthesized using boronate ester I10 as a raw material according to AAV4. Alternatively, the boronic acid corresponding to I10 can be used as a raw material for synthesizing P3.

[0283] An alternative one-pot procedure for the conversion of I9 to P3.

[0284]

[0285] The synthesis of target P3 was performed via a one-pot approach, in which the chloride precursor I9 was directly converted to P3 following the procedure described in AAV5.

[0286] General steps for synthesizing AAV8:

[0287]

[0288] E3.2 (1.10 equiv.), I7.1 (1.00 equiv.), tris(dibenzylideneacetone)dipalladium (Pd) were stirred in toluene at 80° C. under a nitrogen atmosphere. 2 (dba) 3 (0.01 equivalent; CAS: 51364-51-3), tri-tert-butylphosphine (P( t Bu) 3 , CAS: 13716-12-6, 0.04 equiv) and sodium tert-butoxide (NaO t Bu; 1.70 equiv) for 5 h. After cooling to room temperature (rt), the reaction mixture was extracted between toluene and brine, and the phases were separated. 4 The combined organic layers are dried, and the solvent is then removed under reduced pressure. The crude product obtained is purified by recrystallization or column chromatography to obtain I8 as a solid.

[0289] General steps for synthesizing AAV9:

[0290]

[0291] I7.2 (1.10 equiv.), I8 (1.00 equiv.), tris(dibenzylideneacetone)dipalladium (Pd) were stirred in toluene at 110° C. under a nitrogen atmosphere. 2 (dba) 3 (0.01 equivalent; CAS: 51364-51-3), tri-tert-butylphosphine (P( t Bu) 3 , CAS: 13716-12-6, 0.04 equiv) and sodium tert-butoxide (NaO t Bu; 1.70 equiv) for 5 h. After cooling to room temperature (rt), the reaction mixture was extracted between toluene and brine, and the phases were separated. 4 The combined organic layers were dried and the solvent was then removed under reduced pressure. The crude product obtained was purified by recrystallization or column chromatography to obtain I9 as a solid.

[0292] General Synthetic Scheme IV

[0293] General Synthetic Scheme IV provides a synthetic scheme for organic molecules according to the invention, wherein R X =R I , R IX =R II , R VIII =R III , R VII =R IV , and R V =R VI :

[0294]

[0295] The synthesis of the dichloro derivative I2-Cl was carried out as described in AAV2 starting from 1,3-dibromo-2,5-dichlorobenzene (1.0 equiv., CAS: 81067-41-6) and amine I1.

[0296]

[0297] The boronate ester I3-Cl was synthesized from I2-Cl according to the procedure of AAV3, wherein, optionally, trimethyl borate can be used as the borylation reagent to obtain the boronic acid derivative corresponding to I3-Cl.

[0298]

[0299] The p-chloro derivative P1-Cl was synthesized from I3-Cl as described in AAV4.

[0300] Alternatively, under the same conditions, the corresponding boronic acid derivative of substrate I3-Cl can be used as starting material to afford P1-Cl.

[0301] A substituted one-pot ring-closure scheme for directly converting I2-Cl to P1-Cl.

[0302]

[0303] Perform a one-pot synthesis of P1-Cl starting from I2-Cl as described in AAV5.

[0304] General procedure for the synthesis of AAV10:

[0305]

[0306] Under a nitrogen atmosphere, stir compound P1-Cl (1.0 equivalent), boric acid R V -B(OH) 2 (6.0 equivalents), palladium(II) acetate (0.06 equivalent, CAS: 3375-31-3), X-Phos (0.24 equivalent, CAS: 564483-18-7), and tripotassium phosphate (9.0 equivalents, CAS: 7778-53-2) in a mixture of toluene and dioxane (1:1) at 100 °C for 1 hour. After cooling to room temperature (rt), extract the reaction mixture with toluene and water, and separate the phases. Treat the combined organic layers with activated carbon for 10 minutes, then filter through (kieselgur) pad. Dry the filtrate with anhydrous MgSO 4 and then remove the solvent under reduced pressure. Purify the obtained crude product by recrystallization or column chromatography to obtain P1 as a solid.

[0307] General synthesis scheme V

[0308] General synthesis scheme V provides a synthesis scheme for organic molecules according to the invention, wherein R X = R I , R IX = R II , R VIII = R III , R VII = R IV , and R V = R VI :

[0309]

[0310] Synthesize compound I4-Cl according to step AAV6, wherein 1,3-dibromo-2,5-dichlorobenzene (1.0 equivalent, CAS 81067-41-6) and primary amine E1 are used as reactants.

[0311]

[0312] Compound I5-Cl was obtained by using secondary diamine I4-Cl and E2.2 as reactants according to step AAV7.

[0313]

[0314] Borate I6-Cl was obtained by using compound I5-Cl as a raw material according to AAV3. Optionally, trimethyl borate can be used as a boronating reagent under the same conditions to obtain a boric acid derivative corresponding to 16-Cl.

[0315]

[0316] The synthesis of P2-Cl was carried out using I5-Cl as a substrate as described in AAV5.

[0317]

[0318] The target material P2 was synthesized using P2-Cl as a raw material as described in AAV10.

[0319] General synthesis scheme VI

[0320] General synthesis scheme VI provides a synthesis scheme for organic molecules according to the invention, where the limitations of scheme I and scheme II are not applicable (i.e., R X = R I , R IX = R II , R VIII = R III , R VII = R IV , and R V = R VI ).

[0321]

[0322] 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.

[0323]

[0324] Compound I9-Cl was synthesized from I7.2 and I8-Cl according to AAV9.

[0325]

[0326] Synthesis of boronate I10-Cl using precursor I9-Cl as a substrate as described in AAV3. Optionally, trimethyl borate can be used as a boronating reagent to obtain the corresponding boronic acid derivative of I10-Cl.

[0327]

[0328] Synthesis of compound P3-Cl using boronate I10-Cl as a starting material according to AAV4. Optionally, the boronic acid corresponding to I10-Cl can be used as a starting material for the synthesis of P3-Cl.

[0329] Alternative one-pot procedure for the conversion of I9-Cl to P3-Cl.

[0330]

[0331] Synthesis of P3-Cl using I9-Cl as a substrate as described in AAV5.

[0332]

[0333] Synthesis of the target material P3 using P3-Cl as a starting material as described in AAV10.

[0334] Cyclic voltammetry

[0335] Cyclic voltammograms were measured on solutions having a concentration of 10 -3 mol / L of the organic molecule in dichloromethane or a suitable solvent and a suitable supporting electrolyte (e.g., 0.1 mol / L tetrabutylammonium hexafluorophosphate). Measurements were carried out at room temperature under a nitrogen atmosphere using a three-electrode assembly (working electrode and counter electrode: Pt wire, reference electrode: Pt wire), and FeCp 2 / FeCp 2 + was used as an internal standard for calibration. Ferrocene was used as an internal standard to correct the HOMO data for the saturated calomel electrode (SCE).

[0336] Density functional theory calculations

[0337] Molecular structures were optimized using the BP86 functional and the resolution of identity approach (RI). Time-dependent DFT (TD-DFT) methods were used to calculate the excitation energies using the (BP86)-optimized structures. Orbitals and excited state energies were calculated using the B3LYP functional. The Def2-SVP basis set and the m4 grid for the numerical integration method were used. The Turbomole step package was used for all calculations.

[0338] Photophysical measurements

[0339] Sample pretreatment: Spin coating.

[0340] Instrument: Spin150, SPS euro.

[0341] The sample concentration is 10 mg / mL, dissolved in a suitable solvent.

[0342] Steps: 1) 3 seconds at 400 U / min. 2) 20 seconds at 1000 U / min at 1000 Upm / s. 3) 10 seconds at 4000 U / min at 1000 Upm / s. After coating, dry the film at 70 °C for 1 min.

[0343] Photoluminescence spectroscopy and time-correlated single photon counting (TCSPC)

[0344] The steady-state emission spectra were measured by Horiba Scientific Modell FluoroMax-4 equipped with a 150 W xenon arc lamp, excitation and emission monochromators, and a Hamamatsu R928 photomultiplier tube and time-correlated single photon counting option. The emission and excitation spectra were corrected using standard calibration fitting.

[0345] The excited state lifetimes were determined using the TCSPC method with the FM-2013 device and the Horiba Yvon TCSPC hub in the same system.

[0346] Excitation sources:

[0347] Nano LED 370 (wavelength: 371 nm, pulse duration: 1.1 ns)

[0348] Nano LED 290 (wavelength: 294 nm, pulse duration: <1 ns)

[0349] Spectral LED 310 (wavelength: 314 nm)

[0350] Spectral LED 355 (wavelength: 355 nm).

[0351] Data analysis (exponential fitting) was completed using the software suites DataStation and DAS6 analysis software. The fitting was specified using the chi-square test.

[0352] Photoluminescence quantum yield measurement

[0353] For the photoluminescence quantum yield (PLQY) measurement, an absolute PL quantum yield measurement C9920-03G system (Hamamatsu Photonics) was used. The quantum yield and CIE coordinates were determined using software version U6039-05 3.6.0.

[0354] The emission maximum is given in nm, the quantum yield Φ is given in %, and the CIE coordinates are given as x-value, y-value.

[0355] The PLQY was determined using the following protocol:

[0356] 1) Quality assurance: Anthracene (known concentration) in ethanol was used as a reference

[0357] 2) Excitation wavelength: The absorption maximum of the organic molecule was determined and the molecule was excited using this wavelength

[0358] 3) Measurement

[0359] For the sample, the quantum yield of the solution or film was measured under a nitrogen atmosphere. The yield was calculated using the equation:

[0360]

[0361] where n 光子 represents the photon count and Int. represents the intensity.

[0362] Fabrication and characterization of optoelectronic devices

[0363] Optoelectronic devices (specifically, OLED devices) comprising the organic molecules according to the invention can be fabricated via a vacuum evaporation method. If the layer contains more than one compound, the weight percentage of one or more compounds is given in %. The total weight percentage value is 100%, so if no value is given, the fraction of the compound is equal to the difference between the given value and 100%.

[0364] Unoptimized OLEDs were characterized using standard methods and measuring the electroluminescence spectrum, the intensity-dependent external quantum efficiency (in %), which was calculated using the light and current detected by a photodiode. The OLED device lifetime was extracted from the change in luminance during operation at a constant current density. The LT50 value corresponds to the time point at which the measured luminance decreases to 50% of the initial luminance, similarly, the LT80 value corresponds to the time point at which the measured luminance decreases to 80% of the initial luminance, the LT95 value corresponds to the time point at which the measured luminance decreases to 95% of the initial luminance, etc.

[0365] (e.g., applying an increased current density) Accelerated lifetime measurements were performed. For example, the LT80 value at 500 cd / m 2 was determined using the following equation:

[0366]

[0367] where L 0 represents the initial luminance at the applied current density.

[0368] This value corresponds to the average of several (typically 2 to 8) pixels, giving the standard deviation between these pixels.

[0369] HPLC-MS

[0370] HPLC-MS analysis was performed on an Agilent (1100 series) HPLC equipped with an MS detector (Thermo LTQ XL).

[0371] Exemplarily, a typical HPLC method is as follows: In HPLC, an Agilent reverse-phase column 4.6 mm × 150 mm, particle size 3.5 μm (ZORBAX Eclipse Plus C18, 4.6 mm × 150 mm, 3.5 μm HPLC column) was used. HPLC-MS measurements were carried out at room temperature (rt) according to a gradient.

[0372]

[0373] The following solvent mixture was used:

[0374] Solvent A: <![CDATA[H 2 O (90%)]]> MeCN (10%) Solvent B: <![CDATA[H 2 O(10%)]]> MeCN (90%) Solvent C: THF (50%) MeCN (50%)

[0375] A 5 μL injection volume was sampled from a solution with an analyte concentration of 0.5 mg / mL for measurement.

[0376] Ionization of the probe was carried out using an atmospheric pressure chemical ionization (APCI) source in positive (APCI+) or negative (APCI-) ionization mode.

[0377] Example 1

[0378]

[0379] Example 1 was synthesized according to the following steps:

[0380] AAV1 (49% yield), where 4-chlorodiphenylmethane (CAS 831-81-2) was used as reactant E2, and 4-benzylaniline (CAS 1135-12-2) was used as E1;

[0381] AAV2 (42% yield), where 1,3-dibromo-2-chlorobenzene (CAS 19230-27-4) was used as reactant E3;

[0382] And AAV5 (48% yield).

[0383] MS (HPLC-MS, APCI, positive ionization), m / z (retention time): 781.6 (6.16 min).

[0384] The emission maximum of Example 1 (2 wt%, in PMMA) is at 464 nm, the full width at half maximum (FWHM) is 0.17 eV, the CIEy coordinate is 0.12, and the PLQY is 73%. The starting point of the emission spectrum is determined at 2.79 eV.

[0385] Example 2

[0386]

[0387] Example 2 was synthesized according to the following steps:

[0388] AAV1 (49% yield), where 4-chlorodiphenylmethane (CAS 831-81-2) was used as reactant E2, and 4-benzylaniline (CAS 1135-12-2) was used as E1;

[0389] AAV2 (69% yield), where 4-chloro-3,5-dibromotoluene (CAS 202925-05-1) was used as reactant E3;

[0390] And AAV5 (13% yield).

[0391] MS (HPLC-MS, APPI, positive ionization), m / z (retention time): 795.6 (6.26 min).

[0392] The emission maximum of Example 2 (2 wt%, in PMMA) is at 462 nm, the full width at half maximum (FWHM) is 0.17 eV, the CIEy coordinate is 0.11, and the PLQY is 76%. The starting point of the emission spectrum is determined at 2.79 eV.

[0393] Example 3

[0394]

[0395] Example 3 was synthesized according to the following steps:

[0396] AAV2 (83% yield), where 1,3-dibromo-2-chlorobenzene (CAS 19230-27-4) and 4,4'-bis(α,α-dimethylbenzyl)diphenylamine (CAS 10081-67-1) were used as reactants E3 and I1, respectively;

[0397] AAV3 (32% yield), where trimethyl borate (CAS 121-43-7) was used as the boronating reagent, and where the corresponding boric acid derivative of I3 was obtained;

[0398] And AAV4 (23% yield).

[0399] MS (HPLC-MS, APPI, positive ionization), m / z (retention time): 893.7 (7.66 min).

[0400] The emission maximum of Example 3 (2 wt%, in PMMA) is at 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 starting point of the emission spectrum is determined at 2.79 eV.

[0401] Example 4

[0402]

[0403] Example 4 was synthesized according to the following steps:

[0404] AAV2 (72% yield), wherein 4-chloro-3,5-dibromotoluene (CAS 202925-05-1) and 4,4'-bis(α,α-dimethylbenzyl)diphenylamine (CAS 10081-67-1) were used as reactants E3 and I1, respectively;

[0405] AAV3 (50% yield), wherein trimethyl borate (CAS 121-43-7) was used as the boronating reagent, and wherein the corresponding dichloride I2-Cl was used as the reactant, and wherein the corresponding boric acid derivative of I3-Cl was obtained;

[0406] AAV4 (58% yield);

[0407] and AAV10 (81% yield), wherein the corresponding starting material P1-Cl was reacted with boric acid (CAS: 13061-96-6).

[0408] MS (HPLC-MS), m / z (retention time): 907.80 (7.68 min).

[0409] The emission maximum of Example 4 (2 wt%, in PMMA) is at 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 starting point of the emission spectrum is determined at 2.81 eV.

[0410] Example D1

[0411] Example 1 was tested in OLED D1 fabricated with the following layer structure:

[0412]

[0413]

[0414]

[0415] OLED D1 produced an external quantum efficiency (EQE) of 12.1% at 1000 cd / m 2 ². The emission maximum was at 468 nm with an FWHM of 26 nm at 3.6 V. The corresponding CIEy value was 0.12.

[0416] Example D2

[0417] Example 2 was tested in OLED D2 fabricated with the following layer structure:

[0418] Layer number Thickness D2 9 100 nm Al 8 2 nm Liq 7 11 nm NBPhen 6 20 nm MAT1 5 20 nm MAT2 (98%): Example 2 (2%) 4 10 nm MAT3 3 50 nm MAT4 2 7 nm HAT-CN 1 50 nm ITO Substrate Glass

[0419] OLED D2 produced an external quantum efficiency (EQE) of 10.9% at 1000 cd / m 2 ². The emission maximum was at 464 nm with an FWHM of 28 nm at 3.8 V. The corresponding CIEy value was 0.10.

[0420] Example D3

[0421] Example 3 was tested in OLED D3 fabricated with the following layer structure:

[0422]

[0423]

[0424] OLED D3 produced an external quantum efficiency (EQE) of 11.8% at 1000 cd / m 2 ². The emission maximum was at 466 nm with an FWHM of 26 nm at 3.5 V. The corresponding CIEy value was 0.10.

[0425] Example D4

[0426] Example 4 was tested in OLED D4 fabricated with the following layer structure:

[0427] Layer number Thickness D4 9 100 nm Al 8 2 nm Liq 7 11 nm NBPhen 6 20 nm MAT1 5 20 nm MAT2 (98%): Example 4 (2%) 4 10 nm MAT3 3 50 nm MAT4 2 7 nm HAT-CN 1 50 nm ITO Substrate Glass

[0428] OLED D4 produced an external quantum efficiency (EQE) of 11.2% at 1000 cd / m 2 ². The emission maximum was at 464 nm with an FWHM of 26 nm at 3.6 V. The corresponding CIEy value was 0.09.

[0429] Additional examples of the inventive organic molecules

[0430]

[0431]

[0432]

[0433]

[0434]

[0435]

[0436]

Claims

1. An organic molecule, the organic molecule comprising a structure of Formula I: Wherein, Both Ts are Rs 1 or both Vs are Rs 1 , rather than R 1 The group T or the group V, which is not R, is selected from the group consisting of: hydrogen; deuterium; C 1 -C 5 alkyl; and Ph, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu and Ph; Wherein, R 1 comprising or consisting of the structure of formula F: Wherein, n is an integer selected from the group consisting of 0, 1, 2, 3, 4, and 5 each time it appears; and the dashed line indicates the position where Formula F is attached to the structure shown in Formula I; R 6 Each, independently of one another at each occurrence, is selected from the group consisting of: hydrogen; deuterium; and C 1 -C 5 alkyl; R I 、R II 、R III 、R IV 、R V 、R VI 、R VII 、R VIII 、R IX and R X are each 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 ; OSO 2 R 5 ; CF 3 ; CN; halogen; C 1 -C 40 alkyl, optionally substituted with one or more substituents R 5 , and wherein one or more non-adjacent CH 2 groups are optionally substituted with 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, SO 2 , NR 5 , O, S or CONR 5 ; C 1 -C 40 alkoxy, optionally substituted with one or more substituents R 5 , and wherein one or more non-adjacent CH 2 groups are optionally substituted with 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, SO 2 , NR 5 , O, S or CONR 5 substituted; C 1 -C 40 thioalkoxy, optionally substituted with one or more substituents R 5 , and wherein one or more non-adjacent CH 2 groups are optionally replaced by 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, SO 2 , NR 5 , O, S or CONR 5 substituted; C 2 -C 40 alkenyl, optionally substituted with one or more substituents R 5 , and wherein one or more non-adjacent CH 2 groups are optionally replaced by 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, SO 2 , NR 5 , O, S or CONR 5 substituted; C 2 -C 40 alkynyl, optionally substituted with one or more substituents R 5 , and wherein one or more non-adjacent CH 2 groups are optionally replaced by 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, SO 2 , NR 5 , O, S or CONR 5 substituted; C 6 -C 60 aryl, optionally substituted with one or more substituents R 5 ; and C 3 -C 57 heteroaryl, optionally substituted with one or more substituents R 5 ; R 5 Each occurrence is independently selected from the group consisting of: hydrogen; deuterium; OPh; SPh; CF 3 ; CN; F; Si(C 1 -C 5 alkyl) 3 ; Si(Ph) 3 ; C 1 -C 5 alkyl, wherein optionally one or more hydrogen atoms are independently replaced by deuterium, CN, CF 3 or F; C 1 -C 5 alkoxy, wherein optionally one or more hydrogen atoms are independently replaced by deuterium, CN, CF 3 or F; C 1 -C 5 thioalkoxy, wherein optionally one or more hydrogen atoms are independently replaced by deuterium, CN, CF 3 or F; C 2 -C 5 alkenyl, wherein optionally one or more hydrogen atoms are independently replaced by deuterium, CN, CF 3 or F; C 2 -C 5 alkynyl, wherein optionally one or more hydrogen atoms are independently replaced by deuterium, CN, CF 3 or F; C 6 -C 18 aryl, optionally substituted with one or more C 1 -C 5 alkyl substituents; C 3 -C 17 heteroaryl, optionally substituted with one or more C 1 -C 5 alkyl substituents; N(C 6 -C 18 aryl) 2 ; N(C 3 -C 17 heteroaryl) 2 ; and N(C 3 -C 17 heteroaryl)(C 6 -C 18 aryl); and R XI selected from the group consisting of hydrogen, deuterium, chlorine and C 1 -C 5 alkyl groups, Among them, the organic molecule is not 2. The organic molecule according to claim 1, Wherein, R I 、R II 、R III 、R IV 、R V 、R VI 、R VII 、R VIII 、R IX and R X are each independently selected from the group consisting of: R 1 ; hydrogen; deuterium; halogen; Me; i Pr; t Bu; CN; CF 3 ; SiMe 3 ; SiPh 3 ; Ph, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; pyridyl, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; pyrimidinyl, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; carbazolyl, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; triazinyl, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; and N(Ph) 2 .

3. The organic molecule according to claim 1, Wherein, T and V are selected from the group consisting of: R 1 ; hydrogen; deuterium; Me; i Pr; t Bu; and Ph, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu and Ph.

4. The organic molecule according to any one of claims 1 to 3, Wherein, R 6 each independently selected from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; and neopentyl, each time it appears 5. The organic molecule according to any one of claims 1 to 3, Wherein, R 6 Each occurrence is independently selected from the group consisting of: hydrogen; and Me.

6. The organic molecule according to any one of claims 1 to 3, Wherein, R I 、R II 、R III 、R IV 、R V 、R VI 、R VII 、R VIII 、R IX and R X are each independently selected from the group consisting of: R 1 ; hydrogen; deuterium; Me; i Pr; t Bu; Ph, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, and Ph; and N(Ph) 2 .

7. The organic molecule according to any one of claims 1 to 3, the organic molecule comprising a structure of Formula II:

8. The organic molecule according to any one of claims 1 to 3, Wherein, R I , R II , R III and R IV are independently selected from the group consisting of: hydrogen; Me; t Bu; and Ph.

9. The organic molecule according to any one of claims 1 to 3, Wherein, R XI selected from the group consisting of hydrogen, Me, i Pr and t Bu.

10. Use of an organic molecule according to any one of claims 1 to 9 as a light-emitting emitter in an optoelectronic device.

11. The use according to claim 10, Wherein, The optoelectronic device is selected from the group consisting of: Organic light-emitting diodes; Light-emitting electrochemical cells; Organic light-emitting diode sensors; Organic diodes; Organic solar cells; Organic transistors; Organic field-effect transistors; Organic lasers; and Down-conversion elements.

12. A composition, the composition Comprising: (a) An organic molecule according to any one of claims 1 to 9, in the form of an emitter and / or a host; And (b) An emitter and / or a host material different from the organic molecule; and (c) Optionally, dyes and / or solvents.

13. An optoelectronic device, the optoelectronic device comprising an organic molecule according to any one of claims 1 to 9 or the composition according to claim 12, the optoelectronic device being in the form of a device selected from the group consisting of organic light-emitting diodes, light-emitting electrochemical cells, organic light-emitting diode sensors, organic diodes, organic solar cells, organic transistors, organic field-effect transistors, organic lasers, and down-conversion elements.

14. The optoelectronic device according to claim 13, the optoelectronic device Comprising: A substrate; An anode; And A cathode, wherein the anode or the cathode is disposed on the substrate; And A light-emitting layer, disposed between the anode and the cathode and comprising the organic molecule or the composition.

15. A method for manufacturing an optoelectronic device, Wherein, An organic molecule according to any one of claims 1 to 9 or the composition according to claim 12 is used, and the method includes the step of treating the organic molecule by vacuum evaporation or from a solution.

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