Organic molecules for optoelectronic devices

Abstract

The present invention relates to a light-emitting organic molecule, in particular for application in optoelectronic devices. According to the invention, said organic molecule comprises: a first chemical moiety comprising a structure of formula I, and [Chemical formula I] JPEG2025503881000144.jpg4337 - one or two second chemical moieties comprising the structure of formula II: [Chemical formula II] JPEG2025503881000145.jpg5993.

Description

[Technical field]

[0001] The present invention relates to light-emitting organic molecules and their use in organic light-emitting diodes (OLEDs) and other optoelectronic devices. Summary of the Invention [Problem to be solved by the invention]

[0002] The problem that the present invention aims to solve is to provide molecules that are suitable for use in optoelectronic devices. [Means for solving the problem]

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

[0004] According to the invention, the organic molecules are purely organic, i.e. do not contain any metal ions, unlike the metal complexes known to be used in optoelectronic devices. However, the organic molecules of the invention may also contain metalloids, in particular B, Si, Sn, Se and / or Ge. Effect of the Invention

[0005] The organic molecules according to the invention preferably exhibit a maximum emission in the sky blue, green or yellow spectral range, preferably in the green spectral range. The organic molecules preferably exhibit a maximum emission at 470 to 580 nm, preferably 490 to 560 nm, more preferably 500 to 560 nm, even more preferably 510 to 550 nm, most preferably 520 to 540 nm. The photoluminescence quantum yield of the organic molecules according to the invention is preferably 10% or more, more preferably 20% or more, even more preferably 30% or more, in particular 40% or more, particularly preferably 50% or more. The molecules according to the invention in particular exhibit thermally activated delayed fluorescence (TADF). The use of the molecules according to the invention in optoelectronic devices, such as organic light-emitting diodes (OLEDs), leads to an even higher efficiency of the device. The corresponding OLEDs have higher stability than OLEDs with known emitter materials and similar hues and / or, when using the molecules according to the invention in OLED displays, a more accurate reproduction of the hues seen in nature, i.e. a higher resolution in the displayed image, is achieved. In particular, the molecules can be used in combination with fluorescent emitters to enable so-called hyper-fluorescence. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0006] <Organic molecules according to the present invention> An organic molecule according to the present invention comprises or consists of: a first chemical moiety comprising a structure of formula I, and

[0007] [Chemical formula I] JPEG2025503881000002.jpg4337

[0008] One or two a second chemical moiety comprising a structure of formula II,

[0009] [Chemical formula II] JPEG2025503881000003.jpg5993

[0010] Where: n, in each occurrence, is an integer selected from 1 and 2; the first chemical moiety is linked to each of the second chemical moieties through a single bond; T, V, W, X and Y are R 1 and a single bond attachment site linking the first chemical moiety to the second chemical moiety;

[0011] # indicates the binding site between the first chemical moiety and the second chemical moiety; Z, in each occurrence, independently, is a direct bond, CR 3 R 4 , C=CR 3 R 4 , C=O, C=NR 3 , N.R. 3 , O, SiR 3 R 4 , S, S(O) and S(O) 2 is selected from the group consisting of Z § are, in each case, independently of one another, NR 5 , O and S;

[0012] R 1 teeth, are selected, in each case independently from the group consisting of:

[0013] Hydrogen, deuterium, CN, CF 3 , phenyl (Ph),

[0014] C 1 -C 5 Alkyl, wherein optionally one or more hydrogen atoms are replaced with deuterium;

[0015] C 2 -C 8 Alkenyl, wherein optionally one or more hydrogen atoms are replaced with deuterium;

[0016] C 2 -C 8 Alkynyl, wherein optionally one or more hydrogen atoms are replaced with deuterium;

[0017] Optionally, one or more substituents R 5 C replaced with 6 -C 18 Aryl, and

[0018] Optionally, one or more substituents R 5 C replaced with 3 -C 17 Heteroaryl,

[0019] R a , R 3 and R 4 teeth, are selected, in each case independently from the group consisting of:

[0020] hydrogen, deuterium, N(R 5 ) 2 , OR 5 , Si(R 5 ) 3 , B(OR 5 ) 2 , OSO 2 R 5 , CF 3 , C.N., F, Br, I,

[0021] C 1 -C 40 Alkyl, This may optionally include one or more substituents R 5 is replaced by where one or more non-adjacent CH 2 The group is optionally R 5 C=CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO 2 , N.R. 5 , O, S or CONR 5 is replaced by

[0022] C 1 -C 40 Alkoxy, This may optionally include one or more substituents R 5 is replaced by where one or more non-adjacent CH 2 The group is optionally R 5 C=CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO 2 , N.R. 5 , O, S or CONR 5 is replaced by

[0023] C 1 -C 40 Thioalkoxy, This may optionally include one or more substituents R 5 is replaced by where one or more non-adjacent CH 2 The group is optionally R 5 C=CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R5 ) 2 , C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO 2 , N.R. 5 , O, S or CONR 5 is replaced by

[0024] C 2 -C 40 Alkenyl, This may optionally include one or more substituents R 5 is replaced by where one or more non-adjacent CH 2 The group is optionally R 5 C=CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO 2 , N.R. 5 , O, S or CONR 5 is replaced by

[0025] C 2 -C 40 Alkynyl, This may optionally include one or more substituents R 5 is replaced by where one or more non-adjacent CH 2 The group is optionally R 5 C=CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO 2 , N.R. 5 , O, S or CONR 5 is replaced by

[0026] Optionally, one or more substituents R 5 C replaced with 6 -C 60 Aryl, and

[0027] Optionally, one or more substituents R 5 C replaced with 3 -C 57 Heteroaryl,

[0028] R 5 teeth, are selected, in each case independently from the group consisting of:

[0029] Hydrogen, deuterium, N(R 6 ) 2 , OR 6 , Si(R 6 ) 3 , B(OR 6 ) 2 , O.S.O. 2 R 6 , C.F. 3 ,CN,F,Br,I,

[0030] C 1 -C 40 Alkyl, This may optionally include one or more substituents R 6 is replaced by where one or more non-adjacent CH 2 The group is optionally R 6 C=CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO 2 , N.R. 6 , O, S or CONR 6 is replaced by

[0031] C1 -C 40 Alkoxy, This may optionally include one or more substituents R 6 is replaced by where one or more non-adjacent CH 2 The group is optionally R 6 C=CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO 2 , N.R. 6 , O, S or CONR 6 is replaced by

[0032] C 1 -C 40 Thioalkoxy, This may optionally include one or more substituents R 6 is replaced by where one or more non-adjacent CH 2 The group is optionally R 6 C=CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO 2 , N.R. 6 , O, S or CONR 6 is replaced by

[0033] C 2 -C 40 Alkenyl, This may optionally include one or more substituents R 6 is replaced by where one or more non-adjacent CH 2 The group is optionally R 6C=CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO 2 , N.R. 6 , O, S or CONR 6 is replaced by

[0034] C 2 -C 40 Alkynyl, This may optionally include one or more substituents R 6 is replaced by where one or more non-adjacent CH 2 The group is optionally R 6 C=CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO 2 , N.R. 6 , O, S or CONR 6 is replaced by

[0035] Optionally, one or more substituents R 6 C replaced with 6 -C 60 Aryl, and

[0036] Optionally, one or more substituents R 6 C replaced with 3 -C 57 Heteroaryl,

[0037] R 6 teeth, are selected, in each case independently from the group consisting of:

[0038] Hydrogen, deuterium, OPh, CF 3 ,C.N.,F.

[0039] C 1 -C 5 Alkyl, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF 3 or replaced by F,

[0040] C 1 -C 5 Alkoxy, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF 3 or replaced by F,

[0041] C 1 -C 5 Thioalkoxy, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF 3 or replaced by F,

[0042] C 2 -C 5 Alkenyl, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF 3 or replaced by F,

[0043] C 2 -C 5 Alkynyl, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF 3 or replaced by F,

[0044] Optionally, one or more C 1 -C 5 C substituted with alkyl substituents 6 -C 18 Aryl,

[0045] Optionally, one or more C 1 -C 5C substituted with alkyl substituents 3 -C 17 Heteroaryl,

[0046] N(C 6 -C 18 Aryl) 2 ,

[0047] N(C 3 -C 17 Heteroaryl) 2 , and

[0048] N(C 3 -C 17 Heteroaryl)(C 6 -C 18 aryl),

[0049] Where: Substituent R a , R 3 , R 4 or R 5 may independently be one or more substituents R a , R 3 , R 4 or R 5 together optionally forming a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system,

[0050] Where: Exactly one substituent selected from the group T, V, W, X, and Y is a single bond attachment site linking the first chemical moiety to the second chemical moiety; or

[0051] Exactly two of the substituents selected from the group T, V, W, X, and Y are both single bond attachment sites linking the first chemical moiety to one of the second chemical moieties.

[0052] In one embodiment, an organic molecule according to the invention comprises two second chemical moieties, wherein the organic molecule according to the invention comprises or consists of a structure selected from the group consisting of Formula Ia, Formula Ib, Formula Ic, and Formula Id:

[0053] [Chemical formula Ia] JPEG2025503881000004.jpg4340

[0054] [Formula Ib] JPEG2025503881000005.jpg4239

[0055] [Chemical formula Ic] JPEG2025503881000006.jpg4339

[0056] [Chemical formula Id] JPEG2025503881000007.jpg4239

[0057] where § denotes a single bond attachment site linking the first chemical moiety to one of the second chemical moieties.

[0058] In one embodiment, an organic molecule according to the invention comprises one second chemical moiety, wherein the organic molecule according to the invention comprises or consists of a structure selected from the group consisting of Formula IIa, Formula IIb, and Formula IIc:

[0059] [Chemical formula IIa] JPEG2025503881000008.jpg4239

[0060] [Formula IIb] JPEG2025503881000009.jpg4239

[0061] [Chemical formula IIc] JPEG2025503881000010.jpg4339

[0062] where § denotes a single bond attachment site linking a first chemical moiety to a second chemical moiety.

[0063] In a preferred embodiment, an organic molecule according to the present invention comprises or consists of a structure selected from the group consisting of Formula Ia, Formula IIa, and Formula IIc.

[0064] In a preferred embodiment, at least one Z § is NR 5 It is.

[0065] In one embodiment, the second chemical moiety, in each occurrence, independently, is selected from the group consisting of formula IIIa-1:

[0066] [Chemical formula IIIa-1] JPEG2025503881000011.jpg6266.

[0067] In one embodiment, the second moieties, in each occurrence, independently, are selected from the group consisting of formula IIIa-1, where Z § is O or NR 5 It is.

[0068] In one embodiment, Z § In each case, NR 5 It is.

[0069] In one embodiment, the second moiety is, at each occurrence independently, selected from the group consisting of Formula IIIa, Formula IIIb, Formula IIIc, Formula IIIe, Formula IIIf, and Formula IIIg:

[0070] [Chemical formula IIIa] JPEG2025503881000012.jpg6467

[0071] [Chemical formula IIIb] JPEG2025503881000013.jpg4377

[0072] [Chemical formula IIIc] JPEG2025503881000014.jpg5068

[0073] [Chemical formula IIId] JPEG2025503881000015.jpg5968

[0074] [Chemical formula IIIe] JPEG2025503881000016.jpg4576

[0075] [Chemical formula IIIf] JPEG2025503881000017.jpg3680

[0076] [Chemical formula IIIg] JPEG2025503881000018.jpg4580.

[0077] In certain embodiments of the organic molecules of the present invention, Z is a single bond.

[0078] In one embodiment of the present invention, R a are, in each occurrence, independently selected from the group consisting of:

[0079] hydrogen, deuterium, Me, i Pr, t Bu, C.N., CF 3 ,

[0080] 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, Me, i Pr, tBu, CN, CF 3 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; Me, i Pr, t Bu, CN, CF 3 and Ph, Me, i Pr, t Bu, CN, CF 3 N(Ph) optionally substituted with one or more substituents independently selected from the group consisting of 2 .

[0081] In one embodiment of the present invention, R 5 are independently selected from the group consisting of:

[0082] hydrogen, deuterium, Me, i Pr, t Bu, C.N., CF 3 ,

[0083] 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, Me, i Pr, tBu, CN, CF 3 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; Me, i Pr, t Bu, CN, CF 3 and Ph, Me, i Pr, t Bu, CN, CF 3 N(Ph) optionally substituted with one or more substituents independently selected from the group consisting of 2 .

[0084] In one embodiment, R a and R 5 are in each case independently of one another hydrogen (H), methyl (Me), i-propyl (CH(CH 3 ) 2 )( i Pr), t-Butyl ( t Bu), Phenyl (Ph), CN, CF 3 and diphenylamine (NPh 2 ).

[0085] In a preferred embodiment, the second moiety, in each occurrence independently, comprises or consists of a structure according to formula IV:

[0086] [Chemical formula IV] JPEG2025503881000019.jpg6266.

[0087] In a preferred embodiment, the second moiety, in each occurrence independently, comprises or consists of a structure according to formula IVa:

[0088] [Chemical formula IVa] JPEG2025503881000020.jpg8666

[0089] wherein p, in each occurrence, is an integer selected from 1, 2, 3, 4, and 5;

[0090] R 6 are, in each occurrence, independently selected from the group consisting of:

[0091] hydrogen, deuterium, Me, i Pr, t Bu, C.N., CF 3 ,

[0092] 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, Me, i Pr, t Bu, CN, CF 3 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; Me, i Pr, t Bu, CN, CF 3and Ph, Me, i Pr, t Bu, CN, CF 3 N(Ph) optionally substituted with one or more substituents independently selected from the group consisting of 2 .

[0093] In one embodiment, R 6 are, in each occurrence, independently selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu and CN.

[0094] In a preferred embodiment, at least one R 1 is selected from the group consisting of:

[0095] C.N., C.F. 3 , Optionally, one or more substituents R 5 C replaced with 6 -C 18 Aryl, and Optionally, one or more substituents R 5 C replaced with 3 -C 17 Heteroaryl.

[0096] In one embodiment, at least one R 1 is selected from the group consisting of: 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, Me, i Pr,t Bu, CN, CF 3 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, Me, i Pr, t Bu, CN, CF 3 N(Ph) optionally substituted with one or more substituents independently selected from the group consisting of 2 .

[0097] In a preferred embodiment, the organic molecule comprises or consists of a structure selected from the group consisting of:

[0098] [Chemical formula Va] JPEG2025503881000021.jpg4340

[0099] [Chemical formula Vb] JPEG2025503881000022.jpg4340

[0100] [Chemical formula Vc] JPEG2025503881000023.jpg4440

[0101] where § represents a single bond attachment site linking the first chemical moiety to one of the second chemical moieties; R A is selected from the group consisting of: C.N., C.F. 3 , Optionally, one or more substituents R 5 C replaced with 6 -C 18 Aryl, and Optionally, one or more substituents R 5 C replaced with3 -C 17 Heteroaryl, R 2 is hydrogen, deuterium, Me, i Pr, t It is selected from the group consisting of Bu and Ph.

[0102] In one embodiment, R A is selected from the group consisting of:

[0103] JPEG2025503881000024.jpg115141

[0104] JPEG2025503881000025.jpg77141

[0105] JPEG2025503881000026.jpg51141

[0106] JPEG2025503881000027.jpg85141

[0107] JPEG2025503881000028.jpg40141

[0108] JPEG2025503881000029.jpg18141

[0109] JPEG2025503881000030.jpg19141

[0110] JPEG2025503881000031.jpg24122

[0111] JPEG2025503881000032.jpg58141

[0112] Where: The dashed line indicates the substituent R A represents a single bond connecting the group to the remainder of the organic molecule represented by formula I, where two or more adjacent substituents R 5may, independently of one another, optionally form a monocyclic or polycyclic, aliphatic, aromatic and / or benzo-fused ring system, where optionally one or more hydrogen atoms of the ring system thus formed are substituted by R 6 can be substituted with

[0113] In one embodiment, R A are, in each occurrence, independently selected from Group B consisting of the following structures:

[0114] JPEG2025503881000033.jpg67166

[0115] Where: The dashed line indicates the substituent R A represents a single bond connecting the organic molecule represented by formula I, where two or more adjacent substituents R 5 may, independently of one another, optionally form a monocyclic or polycyclic, aliphatic, aromatic and / or benzo-fused ring system, where optionally one or more hydrogen atoms of the ring system thus formed are substituted by R 6 can be substituted with

[0116] <Definition> The term "layer" as used herein refers broadly to a body or sheet-like mass having a planar shape. An optoelectronic device is composed of multiple layers.

[0117] In the context of the present invention, an emissive layer (EML) is a layer of an optoelectronic device, where emission from said layer is observed upon application of a voltage and current to the device. One skilled in the art will appreciate that emission from an optoelectronic device is due to emission from at least one EML. A skilled artisan will appreciate that emission from an EML is typically not (predominantly) due to all materials contained in the EML, but rather due to a particular emitter material.

[0118] In the context of the present invention, an "emitter material" (also referred to as "emitter") is a material which, when included in an emissive layer (EML) of an optoelectronic device, emits light when a voltage and current is applied to the device. Emitter materials are generally "emissive dopant" materials. A dopant material (whether emissive or not) is a material incorporated into a matrix material, referred to herein as a host material, where the host material, when included in an optoelectronic device such as an OLED comprising at least one organic molecule according to the present invention, is generally a H B It is called.

[0119] In the context of the present invention, the term "cyclic group" may be understood in the broadest sense as any monocyclic, bicyclic or polycyclic moiety.

[0120] In the context of the present invention, when referring to a chemical structure, the term "ring" may be understood in the broadest sense as any monocyclic moiety. In the same respect, when referring to a chemical structure, the term "ring" may be understood in the broadest sense as any bicyclic or polycyclic moiety.

[0121] In the context of this invention, a "ring system" may be understood in the broadest sense as any monocyclic, bicyclic or polycyclic moiety.

[0122] In the context of this invention, the term "ring atom" refers to any atom that is part of the cyclic core of a ring or ring system and that is not part of an acyclic substituent optionally attached to the cyclic core.

[0123] In the context of this invention, the term "carbocycle" may be understood in its broadest sense as any cyclic group whose cyclic core structure contains only carbon atoms, which may, of course, be substituted with hydrogen or any other substituent as defined in specific embodiments of this invention. The term "carbocyclic" may be understood as an adjective referring to a cyclic group whose cyclic core structure contains only carbon atoms, which may, of course, be substituted with hydrogen or any other substituent as defined in specific embodiments of this invention.

[0124] In the context of the present invention, the term "heterocycle" can be understood in the broadest sense as any cyclic group whose cyclic core structure contains not only carbon atoms but also at least one heteroatom. The term "heterocyclic" can be understood as an adjective referring to the case where the cyclic core structure is a cyclic group containing not only carbon atoms but also at least one heteroatom. The heteroatoms can be identical or different in each case, unless otherwise specified in a specific embodiment, and can be individually selected from the group consisting of B, Si, N, O, S and Se, more preferably from the group consisting of B, N, O and S, and most preferably from the group consisting of N, O and S. In the context of the present invention, all carbon atoms or heteroatoms contained in the heterocycle can of course be substituted with hydrogen or with any other substituent defined in a specific embodiment of the present invention.

[0125] One of ordinary skill in the art can recognize that any cyclic group (ie, any carbocyclic and heterocyclic ring) may be aliphatic, aromatic or heteroaromatic.

[0126] In the context of the present invention, when referring to a cyclic group (i.e., one ring, multiple rings, ring system, carbocyclic ring, heterocyclic ring), the term "aliphatic" means that the cyclic core structure (not including any optionally attached substituents) contains at least one ring atom that is not part of an aromatic or heteroaromatic ring or ring system. Preferably, most of the ring atoms, more preferably all of the ring atoms in the aliphatic cyclic group are not part of an aromatic or heteroaromatic ring or ring system (e.g., in cyclohexane or piperidine). Here, when referring to an aliphatic ring or ring system in general, no distinction is made between a carbocyclic group and a heterocyclic group, but the term "aliphatic" can be used as an adjective to describe a carbocyclic or heterocyclic ring to indicate whether a heteroatom is included in the aliphatic cyclic group.

[0127] As will be understood by the skilled artisan, the terms "aryl" and "aromatic" may be understood in the broadest sense as any monocyclic, bicyclic, or polycyclic aromatic moiety, i.e., as a ring group in which all ring atoms are part of an aromatic ring system, preferably as part of the same aromatic ring system. However, throughout this application, the terms "aryl" and "aromatic" are restricted to monocyclic, bicyclic, or polycyclic aromatic moieties in which all aromatic ring atoms are carbon atoms. In contrast, in this application, the terms "heteroaryl" and "heteroaromatic" refer to any monocyclic, bicyclic, or polycyclic aromatic moiety in which at least one aromatic carbon ring atom is replaced by a heteroatom (i.e., not carbon). Unless otherwise stated in a particular embodiment of the invention, the at least one heteroatom in a "heteroaryl" or "heteroaromatic" in each instance may be the same or different and may be individually selected from the group consisting of N, O, S, and Se, more preferably from the group consisting of N, O, and S. One of ordinary skill in the art will appreciate that the adjectives "aromatic" and "heteroaromatic" may be used to describe any cyclic group (i.e., any ring system). That is, an aromatic cyclic group (i.e., aromatic ring system) is an aryl group, and a heteroaromatic cyclic group (i.e., heteroaromatic ring system) is a heteroaryl group.

[0128] Unless otherwise specified in a particular embodiment of the present invention, in the present application, an aryl group preferably comprises 6 to 60 aromatic ring atoms, more preferably 6 to 40 aromatic ring atoms, even more preferably 6 to 18 aromatic ring atoms. Unless otherwise specified in a particular embodiment of the present invention, in the present application, a heteroaryl group preferably comprises 5 to 60 aromatic ring atoms, more preferably 5 to 40 aromatic ring atoms, even more preferably 5 to 20 aromatic ring atoms, of which at least one is a heteroatom, preferably selected from N, O, S and Se, more preferably from N, O and S. When one or more heteroatoms comprise a heteroaromatic group, all heteroatoms are preferably selected, independently of one another, from N, O, S and Se, more preferably from N, O and S.

[0129] In the context of this invention, for both aromatic and heteroaromatic groups (e.g., aryl or heteroaryl substituents), the number of aromatic ring carbon atoms is indicated by a subscript in the definition of the particular substituent, e.g., "C 6 -C 60 Aryl" which means that each aryl substituent contains from 6 to 60 aromatic carbon ring atoms. The same subscript numbers are used to indicate the number of carbon atoms permitted in all other types of substituents, whether aliphatic, aromatic, or heteroaromatic. For example, "C 1 -C 40 The term "alkyl" refers to an alkyl substituent containing from 1 to 40 carbon atoms.

[0130] Preferred examples of aryl groups include groups derived from benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, fluoranthene, benzanthracene, benzophenanthrene, tetracene, pentacene, benzopyrene, or combinations of such groups.

[0131] Preferred examples of heteroaryl groups are furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene; pyrrole, indole, isoindole, carbazole, indolocarbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthoimidazole, phenanthroimidazole, pyridoimidazole, pyrazinoimidazole, quinoxalinoimidazole, oxazole, benzoxazole, naphthoxazole, anthroxazole, These include groups derived from phenanthroxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-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, 1,2,4,5-tetrazine, purine, pteridine, indolizine and benzothiadiazole, or combinations of these groups.

[0132] The term "arylene" as used throughout this application refers to a divalent aryl substituent that possesses two attachment sites and serves as a linker structure to another molecular structure. In the same vein, the term "heteroarylene" refers to a divalent aryl substituent that possesses two attachment sites and serves as a linker structure to another molecular structure.

[0133] In the context of the present invention, when referring to an aromatic or heteroaromatic ring system, the term "fused" means that the "fused" aromatic or heteroaromatic rings share at least one bond that is part of both ring systems. For example, naphthalene (or naphthyl when referred to as a substituent) or benzothiophene (or benzothiophenyl when referred to as a substituent) is considered to be a fused aromatic ring system in the context of the present invention, where two benzene rings (in the case of naphthalene) or thiophene and benzene (in the case of benzothiophene) share one bond. Also, in such a context, sharing a bond can be understood to include sharing the two atoms that constitute each bond, and a fused aromatic or heteroaromatic ring system can be understood as one aromatic or heteroaromatic system. Also, one or more bonds can be understood to be shared by the aromatic or heteroaromatic rings that constitute the fused aromatic or heteroaromatic ring system (e.g., in pyrene). Aliphatic ring systems may also be fused, which will be understood to have the same meaning as aromatic or heteroaromatic ring systems, except, of course, that a fused aliphatic ring system is not aromatic. An aromatic or heteroaromatic ring system may also be fused (i.e., share at least one bond) with an aliphatic ring system.

[0134] In the context of this invention the term "condensed" ring system has the same meaning as a "fused" ring system.

[0135] In certain embodiments of the invention, adjacent substituents attached to a ring or ring system can form a further monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system fused to the aromatic or heteroaromatic ring or ring system to which said substituents are attached. Optionally, the fused ring system so formed can be understood to be larger (meaning containing more ring atoms) than the aromatic or heteroaromatic ring or ring system to which the adjacent substituents are attached. In that case (and when such a number is provided), the "total" number of ring atoms contained in the fused ring system should be understood to be the sum of the ring atoms contained in the aromatic or heteroaromatic ring or ring system. Although adjacent substituents are bonded and the ring atoms of the additional ring system are formed by the adjacent substituents, the ring atoms shared by the fused rings are counted once, not twice. For example, a benzene ring can have two adjacent substituents forming yet another benzene ring, such that a naphthalene core is formed. The naphthalene core contains 10 ring atoms because the two carbon atoms shared by the two benzene rings are counted only once, not twice. In this context, the term "adjacent substituents" means substituents that are attached to the same or adjacent atoms.

[0136] Generally, in the context of the present invention, the term "adjacent substituents" or "adjacent groups" means substituents or groups which are attached to the same or adjacent atoms.

[0137] In the context of the present invention, the term "alkyl group" is understood in the broadest sense as any linear, branched or cyclic alkyl substituent. In particular, the term "alkyl" refers to the substituents methyl (Me), ethyl (Et), n-propyl (N-propyl ... ethyl (Et), ethyl (Et), ethyl (Et), ethyl (Et), ethyl (Et), ethyl (Et), ethyl (Et), ethyl (Et), ethyl (Et), ethyl (E n Pr), i-propyl ( i Pr), cyclopropyl, n-butyl ( n Bu), i-Butyl ( i Bu), s-Butyl ( s Bu), t-Butyl ( tBu), cyclobutyl, 2-methylbutyl, n-pentyl, s-pentyl, t-pentyl, 2-pentyl, neo-pentyl, cyclopentyl, n-hexyl, s-hexyl, t-hexyl, 2-hexyl, 3-hexyl, neo-hexyl, cyclohexyl, 1-methylcyclopentyl, 2-methylpentyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, cycloheptyl, 1-methylcyclohexyl, n-octyl, 2-ethylhexyl, cyclooctyl, 1-bicyclo[2,2,2]octyl, 2-bicyclo[2,2,2]octyl, 2-(2,6-dimethyl)octyl, 3-(3,7-dimethyl)octyl, adamantyl, 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-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 -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,These include 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.

[0138] For example, in s-butyl, s-pentyl, and s-hexyl, the "s" means "secondary", i.e., s-butyl, s-pentyl, and s-hexyl are equivalent to sec-butyl, sec-pentyl, and sec-hexyl, respectively. For example, in t-butyl, t-pentyl, and t-hexyl, the "t" means "tertiary", i.e., t-butyl, t-pentyl, and t-hexyl are equivalent to tert-butyl, tert-pentyl, and tert-hexyl, respectively.

[0139] As used throughout this specification, the term "alkenyl" includes straight-chain, branched and cyclic alkenyl substituents. The term "alkenyl group" includes, for example, the substituents ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl or cyclooctadienyl.

[0140] As used throughout this specification, the term "alkynyl" includes straight-chain, branched and cyclic alkynyl substituents. The term "alkynyl group" includes, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl.

[0141] As used throughout this specification, the term "alkoxy" includes straight chain, branched and cyclic alkoxy substituents. The term "alkoxy group" includes, for example, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy and 2-methylbutoxy.

[0142] The term "thioalkoxy" as used throughout this specification includes straight-chain, branched and cyclic thioalkoxy substituents, in which the oxygen atom O of the corresponding alkoxy group is replaced by S.

[0143] The term "halogen" (or "halo" when referring to a substituent in chemical nomenclature) as used throughout this specification may be understood in its broadest sense to be any atom of an element in the seventh main group (i.e., group 17) of the Periodic Table of the Elements, preferably fluorine, chlorine, bromine or iodine.

[0144] When a molecular fragment is described as being attached to a substituent or other moiety, the name may be described as just the fragment (e.g., naphthyl, dibenzofuryl) or as the whole molecule (e.g., naphthalene, dibenzofuran). As used herein, the above modes of describing a substituent or attached fragment are considered equivalent.

[0145] In addition, in this application, "C 6 -C 60 aryl" or "C 1 -C 40 Whenever a substituent such as "alkyl" is referred to without a name indicating the point of attachment within that substituent, this means that the respective substituent may be attached via any atom. For example, "C 6 -C 60 "Aryl" substituents are attached via any 6 to 60 aromatic carbon atoms and are defined as "C 1 -C 40An "alkyl" substituent may be attached via any 1 to 40 aliphatic carbon atoms, while a "2-cyanophenyl" substituent is attached only in a manner such that its CN group is adjacent to the point of attachment in a manner that allows for accurate chemical nomenclature.

[0146] In the context of the present invention, whenever a substituent such as "butyl", "biphenyl" or "terphenyl" is mentioned without further details, this means that any isomer of the respective substituent is acceptable for that particular substituent. In this regard, for example, the term "butyl" as a substituent includes n-butyl, s-butyl, t-butyl and iso-butyl as substituents. Similarly, the term "biphenyl" as a substituent includes ortho-biphenyl, meta-biphenyl or para-biphenyl, where ortho, meta and para are defined with respect to the site of attachment of the biphenyl substituent to the respective chemical moiety carrying the biphenyl substituent. Similarly, the term "terphenyl" includes as substituents 3-ortho-terphenyl, 4-ortho-terphenyl, 4-meta-terphenyl, 5-meta-terphenyl, 2-para-terphenyl or 3-para-terphenyl, where ortho, meta and para indicate the positions of the two Ph moieties in the terphenyl group relative to each other, and "2-", "3-", "4-" and "5-" indicate the positions of attachment of the terphenyl substituent to the respective chemical moieties bearing the terphenyl substituent, as known to the skilled artisan.

[0147] It is understood that all of the groups, and indeed all chemical moieties, defined above, whether cyclic or acyclic, aliphatic, aromatic or heteroaromatic, may be further substituted by specific embodiments described herein.

[0148] In exemplary embodiments, where a group is defined differently from the general definition given herein, the definition in this embodiment applies.

[0149] All hydrogen atoms (H) contained in any structure referred to in this application may be replaced, in each case independently of one another, by deuterium (D), unless specifically stated otherwise. The replacement of hydrogen with deuterium is common practice and will be apparent to those skilled in the art.

[0150] When comparing experimental or calculated data, values ​​must be determined by the same methodology. For example, a specified method must be used to determine the experimental ΔE ST is determined to be less than 0.4 eV, comparisons are only valid if the same specific method involving the same conditions is used. To give a specific example, a comparison of the photoluminescence quantum yields (PLQY) of different compounds is only valid if the PLQY determinations are made using the same protocol under the same reaction conditions (e.g., measurements at room temperature on 10% PMMA film). Also, the calculated energy values ​​must be determined using the same calculation method (with the same functions and the same basis set).

[0151] Superfluorescence is a concept related to light emission from optoelectronic devices, especially OLEDs, where at least one emissive layer comprises one or more TADF materials and one or more fluorescent emitters. In superfluorescence, at least one TADF material can convert a triplet excited state to a singlet excited state by reverse-intersystem-crossing (RISC) and emit light after transferring the excitation energy to at least one fluorescent emitter. This can allow for the harvesting of triplet excitons for efficient fluorescence generation.

[0152] <Optoelectronic device containing organic molecules according to the present invention> A further aspect of the invention relates to an optoelectronic device comprising an organic molecule according to the invention.

[0153] In one embodiment, the optoelectronic device comprising the organic molecule according to the present invention is selected from the group consisting of: Organic Light Emitting Diode (OLED), Light-emitting electrochemical cells, OLED sensors, especially gas and steam sensors that are not completely isolated from the outside, Organic diodes, ·Organic solar cells, Organic transistors, Organic field-effect transistors, Organic lasers, and Down conversion element.

[0154] The light-emitting electrochemical cell consists of three layers: a cathode, an anode, and an active layer comprising the organic molecules according to the invention.

[0155] In a preferred embodiment, the optoelectronic device comprising the organic molecules according to the invention is selected from the group consisting of an organic light emitting diode (OLED), a light emitting electrochemical cell (LEC), an organic laser and a light emitting transistor.

[0156] In a more preferred embodiment, the optoelectronic device comprising the organic molecules according to the present invention is an organic light emitting diode (OLED).

[0157] In one embodiment, the optoelectronic device comprising the organic molecules according to the invention is an OLED having the following layer structure:

[0158] 1. Substrate 2. Anode layer A 3. Hole injection layer (HIL) 4. Hole transport layer (HTL) 5.Electron blocking layer (EBL) 6. Emitting layer (EML) 7. Hole Blocking Layer (HBL) 8.Electron transport layer (ETL) 9.Electron injection layer (EIL) 10. Cathode layer C

[0159] Here, the OLED (having an inverted stack layer structure) optionally includes each layer except for the anode layer A, the cathode layer C, and the light-emitting layer EML, and different layers may be combined, and the OLED may include one or more layers of each layer type defined above.

[0160] Optoelectronic devices comprising at least one organic molecule according to the present invention may also optionally comprise one or more protective layers to protect the device from damaging exposure to harmful substances in the environment including, for example, moisture, vapor and / or gas.

[0161] In one embodiment of the present invention, the optoelectronic device comprising the organic molecules according to the present invention is an OLED having the following inverted layer structure:

[0162] 1. Substrate 2. Cathode layer C 3.Electron injection layer (EIL) 4.Electron transport layer (ETL) 5. Hole Blocking Layer (HBL) 6. Emitting layer (EML) 7.Electron blocking layer (EBL) 8. Hole transport layer (HTL) 9. Hole injection layer (HIL) 10. Anode layer A

[0163] Here, the OLED optionally includes each layer except for the anode layer A, the cathode layer C, and the light-emitting layer EML, and different layers may be combined, and the OLED may include one or more layers of each layer type defined above.

[0164] The organic molecules according to the invention (according to the above-mentioned embodiments) can be used in various layers depending on the specific structure and substitution. When used, in each layer of the optoelectronic device, in particular the OLED, the fraction of the organic molecules according to the invention is 0.1 to 99% by weight, more particularly 1 to 80% by weight. In an alternative embodiment, in each layer, the proportion of the organic molecules is 100% by weight.

[0165] In one embodiment, the optoelectronic device comprising the organic molecules according to the present invention is an OLED that can have a stacked structure. In said structure, individual units are stacked on top of each other, unlike the common arrangement in which OLEDs are arranged side by side. Mixed light can be generated by an OLED that exhibits a stacked structure, and in particular, white light can be generated by stacking a blue OLED, a green OLED and a red OLED. An OLED that exhibits a stacked structure may also optionally include a charge generation layer (CGL), which is generally located between two OLED subunits and is generally configured as an n-doped layer and a p-doped layer. Generally, the n-doped layer of one CGL is located closer to the anode layer.

[0166] In one embodiment, the optoelectronic device comprising the organic molecules according to the present invention is an OLED comprising two or more light-emitting layers between an anode and a cathode.In particular, the so-called tandem OLED comprises three light-emitting layers, where one light-emitting layer emits red light, one light-emitting layer emits green light, and one light-emitting layer emits blue light, and may optionally comprise additional layers between each light-emitting layer, such as a charge generation layer, a charge blocking layer, or a charge transport layer.In a further embodiment, the light-emitting layers are stacked adjacently.In a further embodiment, the tandem OLED comprises a charge generation layer between each two light-emitting layers.Also, adjacent light-emitting layers or light-emitting layers separated by a charge generation layer can be merged.

[0167] In one embodiment, an optoelectronic device comprising an organic molecule according to the invention is also an essentially white optoelectronic device, meaning that the device emits white light. For example, such a white optoelectronic device may also comprise at least one (deep) blue emitter molecule and one or more emitter molecules emitting green light and / or red light. There may then optionally be an energy transfer between the two or more molecules, as described later in this text.

[0168] In the case of an optoelectronic device comprising an organic molecule according to the invention, at least one organic molecule according to the invention is included in the light-emitting layer (EML) of the optoelectronic device, most preferably in the EML of an OLED. However, the organic molecule according to the invention is also used, for example, in an electron transport layer (ETL) and / or an electron blocking layer (EBL) or an exciton blocking layer and / or a hole transport layer (HTL) and / or a hole blocking layer (HBL). When used, the fraction of the organic molecule according to the invention in each layer of the optoelectronic device, in particular in the OLED, is 0.1 to 99% by weight, more particularly 1 to 80% by weight. In an alternative embodiment, in each layer, the proportion of the organic molecule is 100% by weight.

[0169] The selection criteria for materials suitable for the individual layers of optoelectronic devices, in particular OLEDs, form part of the common knowledge of the person skilled in the art. The state of the art indicates many substances used for the individual layers, informing which substances are suitable for use together with each other. It is understood that any substance used in the state of the art can also be used in optoelectronic devices comprising organic molecules according to the invention. Below, preferred examples of substances for the individual layers will be given. As mentioned above, it is understood that this does not mean that all types of layers listed below must be present in an optoelectronic device comprising at least one organic molecule according to the invention. Furthermore, it is understood that an optoelectronic device comprising at least one organic molecule according to the invention comprises one or more of the respective layers listed below, such as for example two or more light-emitting layers (EMLs). It can be understood that two or more layers of the same type (for example two or more EMLs, or two or more HTLs) do not necessarily comprise the same materials, or even the same materials in the same proportions. Also, an optoelectronic device comprising at least one organic molecule according to the invention does not necessarily comprise all the types of layers listed below, where an anode layer, a cathode layer and an emissive layer are generally present in all cases.

[0170] The substrate can be made of any material or composition of materials. Most frequently, a glass slide is used as the substrate. Alternatively, a thin metal layer (e.g. copper, gold, silver or aluminum film) or a plastic film or plastic slide can be used, which allows a higher level of flexibility. The anode layer A is made of a material that allows a film to be obtained that is mostly (essentially) transparent. Since at least one of the two electrodes must be (essentially) transparent to allow light emission from the OLED, one of the anode layer A or the cathode layer C is transparent. Preferably, the anode layer A is rich in or consists of transparent conductive oxides (TCOs). Such an anode layer A may comprise, 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.

[0171] Preferably, the anode layer A is (essentially) indium tin oxide (ITO) (e.g., (InO 3 ) 0.9 (SnO 2 ) 0.1 The roughness of the anode layer A due to the transparent conducting oxide (TCO) can be mitigated by using a hole injection layer (HIL). The HIL also facilitates the injection of similar charge carriers (i.e. holes) in that the transport of similar charge carriers from the TCO to the hole transport layer (HTL) is promoted. The hole injection layer (HIL) can be made of poly-3,4-ethylenedioxythiophene (PEDOT), polystyrenesulfonic acid (PSS), MoO 2 , V 2 O 5, CuPC or CuI, in particular a mixture of PEDOT and PSS. The hole injection layer (HIL) can also prevent diffusion of metals from the anode layer A into the hole transport layer (HTL). For example, the HIL can be poly-3,4-ethylenedioxythiophene:polystyrenesulfonate (PEDOT:PSS), poly-3,4-ethylenedioxythiophene (PEDOT), 4,4',4"-tris[phenyl(m-tolyl)amino]triphenylamine (mMTDATA), 2,2',7,7'-tetrakis(n,n-diphenylamino)-9,9'-spirobifluorene (Spiro-TAD), N1,N1'-(biphenyl-4,4'-diyl)bis(N1-phenyl-N4,N4-di-m-tolylbenzene-1,4-diamine (DNTPD), N,N'-nis-(1-naphthalene-2-yl)phenylamine (NAPH), N,N'-bis ... N,N'-triphenyl-N,N'-bis-(1,1'-biphenyl)-4,4'-diamine (NPB), N,N'-diphenyl-N,N'-di-[4-(N,N-diphenylamino)phenyl]benzidine (NPNPB), N,N,N',N'-tetrakis(4-methoxyphenyl)benzidine (MeO-TPD), 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN) and / or N,N'-diphenyl-N,N'-bis-(1-naphthyl)-9,9'-spirobifluorene-2,7-diamine (Spiro-NPD).

[0172] Adjacent to the anode layer A or the hole injection layer (HIL) is generally a hole transport layer (HTL). Any hole transport compound can be used here. For example, electron-rich heteroaromatic compounds such as triarylamines and / or carbazoles can be used as hole transport compounds. The HTL can reduce the energy barrier between the anode layer A and the light-emitting layer (EML). The hole transport layer (HTL) is also an electron blocking layer (EBL). Preferably, the hole transport compound has a lowest excited triplet state T1 with a relatively high energy level. For example, the hole transport layer (HTL) may be formed of a material selected from the group consisting of tris(4-carbazolyl-9-ylphenyl)amine (TCTA), poly(4-butylphenyl-diphenylamine) (poly-TPD), poly(4-butylphenyl-diphenylamine) (α-NPD), 4,4'-cyclohexylidene-bis[N,N-bis(4-methylphenyl)benzeneamine] (TAPC), 4,4',4"-tris[2-naphthyl(phenyl)-amino]triphenylamine (2-TNATA), 2,2',7,7'-tetrakis(n,n-diphenylamino)-9,9'-spirobifluorene (Spiro-TAD), N1,N1'-(biphenyl-4,4'-diyl)bis(N1-phenyl-N4,N4-di-m-tolylbenzene-1,4-diamine (DNTPD), N,N'-bis-(1-naphthyl)benzene-2,4-diamine (DNTPD), N,N'-bis-(1-naphthyl) ... The HTL may comprise a star-shaped heterocyclic compound such as N,N'-phenyl-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine (NPB), N,N'-diphenyl-N,N'-di-[4-(N,N-diphenylamino)phenyl]benzidine (NPNPB), N,N,N',N'-tetrakis(4-methoxyphenyl)benzidine (MeO-TPD), 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN) and / or 9,9'-diphenyl-6-(9-phenyl-9H-carbazol-3-yl)-9H,9'H-3,3'-bicarbazole (TrisPcz). The HTL may also comprise a p-doped layer which may consist of an inorganic or organic dopant in an organic hole transport matrix.The inorganic dopant may be, for example, a transition metal oxide such as vanadium oxide, molybdenum oxide, or tungsten oxide. The organic dopant may be, for example, tetrafluorotetracyanoquinodimethane (F. 4 -TCNQ), copper-pentafluorobenzoate (Cu(I)pFBz) or transition metal complexes can be used.

[0173] The EBL can include, for example, 1,3-bis(carbazol-9-yl)benzene (mCP), tris(4-carbazolyl-9-ylphenyl)amine (TCTA), 4,4′,4″-tris[2-naphthyl(phenyl)amino]triphenylamine (2-TNATA), 3,3-di(9H-carbazol-9-yl)biphenyl (mCBP), 9-phenyl-3,6-bis(9-phenyl-9H-carbazol-3-yl)-9H-carbazole (tris-Pcz), 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CzSi), and / or N,N′-dicarbazolyl-1,4-dimethylbenzene (DCB).

[0174] Adjacent to the hole transport layer (HTL) or (if present) the electron blocking layer (EBL) is typically the light emitting layer (EML). The light emitting layer (EML) contains at least one light emitting molecule (i.e., emitter material). The EML typically further contains one or more host materials (also called matrix materials). For example, the host material may be 4,4'-bis-(N-carbazolyl)-biphenyl (CBP), 1,3-bis(carbazol-9-yl)benzene (mCP), 3,3-di(9H-carbazol-9-yl)biphenyl (mCBP), dibenzo[b,d]thiophen-2-yltriphenylsilane (Sif87), 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CzSi), dibenzo[b,d]thiophen-2-yl)diphenylsilane (Sif88), bis[2-(diphenylphosphino)phenyl]etheroxide (DPEPO), 9-[3-(dibenzofuran-2-yl)phenyl]-9H carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole, 2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine (T2T), 2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine (T3T) and / or 2,4,6-tris(9,9'-spirobifluoren-2-yl)-1,3,5-triazine (TST). As known to those skilled in the art, host materials should generally be selected to exhibit a first (i.e., lowest) excited triplet state (T1) and a first (i.e., lowest) excited singlet state (S1) energy level that is higher in energy than the first (i.e., lowest) excited triplet state (T1) and the first (i.e., lowest) excited singlet state (S1) energy level of at least one emissive molecule incorporated into the respective host material.

[0175] As mentioned above, in the context of the present invention, it is preferred that at least one EML of an optoelectronic device comprises at least one molecule according to the invention. Preferred compositions of EMLs of optoelectronic devices comprising at least one organic molecule according to the invention are explained in more detail in a later section of the text (see below).

[0176] Adjacent to the light-emitting layer (EML) may be an electron-transporting layer (ETL). Any electron-transporting material may be used here. Exemplarily, electron-deficient compounds such as benzimidazole, pyridine, triazole, triazine, oxadiazole (e.g., 1,3,4-oxadiazole), phosphine oxides, and sulfones may be used. The electron-transporting material may also be a star-shaped heterocyclic compound such as 1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl (TPBi). The ETL may be, for example, 2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), aluminum-tris(8-hydroxyquinoline) (Alq 3 ), diphenyl-4-triphenylsilylphenyl-phosphine oxide (TSPO1), 2,7-di(2,2'-bipyridin-5-yl)triphenyl (BPyTP2), dibenzo[b,d]thiophen-2-yltriphenylsilane (Sif87), dibenzo[b,d]thiophen-2-yl)diphenylsilane (Sif88), 1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene (BmPyPhB), and / or 4,4'-bis-[2-(4,6-diphenyl-1,3,5-triazinyl)]-1,1'-biphenyl (BTB). Optionally, the ETL can be doped with a material such as 8-hydroxyquinolinolatolithium (Liq). The electron transport layer (ETL) can also block holes. Alternatively, a hole blocking layer (HBL) is typically introduced between the EML and the ETL.

[0177] The hole blocking layer (HBL) may be, for example, BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline = bathocuproine), 4,6-diphenyl-2-(3-(triphenylsilyl)phenyl)-1,3,5-triazine, 9,9'-(5-(6-([1,1'-biphenyl]-3-yl)-2-phenylpyrimidin-4-yl)-1,3-phenylene)bis(9H-carbazole), bis(8-hydroxy-2-methylquinoline)-(4-phenylphenoxy)aluminum (BAlq), 2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), aluminum-tris(8-hydroxyquinoline) (Alq 3 ), diphenyl-4-triphenylsilylphenyl-phosphine oxide (TSPO1), 2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine (T2T), 2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine (T3T), 2,4,6-tris(9,9'-spirobifluoren-2-yl)-1,3,5-triazine (TST), and / or 1,3,5-tris(N-carbazolyl)benzene / 1,3,5-tris(carbazol-9-yl)benzene (TCB / TCP).

[0178] Adjacent to the electron transport layer (ETL) may be a cathode layer C. The cathode layer C may, for example, comprise or consist of a metal (e.g. Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, LiF, Ca, Ba, Mg, In, W or Pd) or a metal alloy. For practical reasons, the cathode layer C may be composed of an (essentially) opaque metal such as Mg, Ca or Al. Alternatively or additionally, the cathode layer C may also comprise graphite and / or carbon nanotubes (CNTs). Alternatively, the cathode layer C may comprise or consist of nanoscale silver wires.

[0179] An OLED comprising at least one organic molecule according to the invention may optionally further comprise a protective layer, also called an electron injection layer (EIL), between the electron transport layer (ETL) and the cathode layer C. Such layers include lithium fluoride, cesium fluoride, silver, 8-hydroxyquinolinolatolithium (Liq), Li 2 O, BaF 2 , MgO and / or NaF.

[0180] Optionally, the electron transport layer (ETL) and / or the hole blocking layer (HBL) can also comprise one or more host compounds.

[0181] As used herein, unless more specifically defined in a particular context, the designations for the hue of emitted and / or absorbed light are as follows:

[0182] Purple: >380~420nm wavelength range Deep blue: wavelength range >420~480nm Sky blue: Wavelength range >480~500nm Green: >500~560nm wavelength range Yellow: >560~580nm wavelength range Orange: >580~620nm wavelength range Red: Wavelength range of >620~800nm.

[0183] Associated with the emitter molecule (i.e., emitter material), such a hue indicates the maximum emission of the primary emission peak. Thus, for example, a deep blue emitter has a maximum emission in the range >420-480 nm, a sky blue emitter has a maximum emission in the range >480-500 nm, a green emitter has a maximum emission in the range >500-560 nm, and a red emitter has a maximum emission in the range >620-800 nm.

[0184] The deep blue emitter may have a maximum emission preferably below 475 nm, more preferably below 470 nm, even more preferably below 465 nm, or even less than 460 nm. It is generally above 420 nm, preferably above 430 nm, more preferably above 440 nm, or even more preferably above 450 nm. In one embodiment, the organic molecules according to the invention generally exhibit a maximum emission of 420 to 500 nm, more preferably 430 to 490 nm, even more preferably 440 to 480 nm, and most preferably 450 to 470 nm, measured at room temperature (i.e. (about) 20° C.) from a spin-coated film containing 10% by weight of the organic molecules according to the invention in poly(methyl methacrylate) (PMMA).

[0185] Yet another embodiment relates to an OLED comprising at least one organic molecule according to the present invention and emitting light having CIEx and CIEy color coordinates close to the CIEx (=0.131) and CIEy (=0.046) color coordinates of primary blue (CIEx=0.131 and CIEy=0.046) as defined by ITU-R Recommendation BT.2020 (Rec.2020), which is suitable for use in UHD (Ultra High Definition) displays, e.g. UHD-TV. Thus, a further aspect of the present invention relates to an OLED comprising at least one organic molecule according to the present invention, the emission of which exhibits CIEx colour coordinates of 0.02 to 0.30, preferably 0.03 to 0.25, more preferably 0.05 to 0.20, even more preferably 0.08 to 0.18 or even more preferably 0.10 to 0.15 and / or CIEy colour coordinates of 0.00 to 0.45, preferably 0.01 to 0.30, more preferably 0.02 to 0.20, even more preferably 0.03 to 0.15 or even more preferably 0.04 to 0.10.

[0186] Yet another embodiment has a luminance of 1000 cd / m 2and / or an external quantum efficiency of more than 8%, preferably more than 10%, more preferably more than 13%, even more preferably more than 15% or even more preferably more than 20%; and / or an emission maximum between 420 nm and 500 nm, more preferably between 430 nm and 490 nm, even more preferably between 440 nm and 480 nm, and most preferably between 450 nm and 470 nm; and / or an emission maximum of less than 500 cd / m 2 The present invention relates to an OLED comprising at least one organic molecule according to the present invention, which exhibits a LT80 value of more than 100 h, preferably more than 200 h, more preferably more than 400 h, even more preferably more than 750 h, or even more than 1000 h.

[0187] The green emitter material may preferably have an emission maximum of 500 to 560 nm, more preferably 510 to 550 nm, even more preferably 520 to 540 nm. In a preferred embodiment, the organic molecules according to the invention generally exhibit an emission maximum of 500 to 560 nm, more preferably 510 to 550 nm, most preferably 520 to 540 nm, measured at room temperature (i.e. (about) 20° C.) from a spin-coated film comprising 10% by weight of the organic molecules according to the invention in poly(methyl methacrylate) (PMMA).

[0188] Yet another embodiment relates to an OLED comprising at least one organic molecule according to the present invention and emitting light having CIEx and CIEy color coordinates close to the CIEx (=0.170) and CIEy (=0.797) color coordinates of primary green (CIEx=0.170 and CIEy=0.797) as defined by ITU-R Recommendation BT.2020 (Rec.2020), which is suitable for use in UHD displays, e.g., UHD-TV. The term "close" in this paragraph refers to the range of CIEx and CIEy color coordinates provided at the end of this paragraph. While in commercial applications, typically a top light-emitting element (top electrode is transparent) is used, the test element used throughout the present invention shows a bottom light-emitting element (bottom electrode and substrate are transparent). Thus, a further aspect of the present invention relates to an OLED comprising at least one organic molecule according to the present invention, the emission of which exhibits CIEx colour coordinates of 0.10 to 0.45, preferably 0.10 to 0.35, more preferably 0.10 to 0.30, even more preferably 0.10 to 0.25 or very particularly 0.15 to 0.20 and / or CIEy colour coordinates of 0.60 to 0.92, preferably 0.65 to 0.90, more preferably 0.70 to 0.88, even more preferably 0.75 to 0.86 or very particularly 0.79 to 0.84.

[0189] Yet another preferred embodiment has a luminance of 14500 cd / m 2 and / or an external quantum efficiency of more than 10%, preferably more than 13%, more preferably more than 15%, even more preferably more than 17%, or even more preferably more than 20%; and / or an emission maximum of 500 to 560 nm, preferably 510 to 550 nm, more preferably 520 to 540 nm, and / or an emission maximum of 14500 cd / m 2 The present invention relates to an OLED comprising at least one organic molecule according to the present invention, which exhibits a LT97 value of more than 100 h, preferably more than 250 h, more preferably more than 500 h, even more preferably more than 750 h, or even more preferably more than 1000 h.

[0190] Yet another preferred embodiment concerns an OLED comprising at least one organic molecule according to the invention and emitting at a well-defined color point. Preferably, the OLED emits light with a narrow emission band (small full width at half maximum (FWHM)). In a preferred embodiment, the OLED comprising at least one organic molecule according to the invention emits light with a FWHM of the main emission peak of less than 0.50 eV, preferably less than 0.48 eV, more preferably less than 0.45 eV, more preferably less than 0.43 eV, more preferably less than 0.40 eV, more preferably less than 0.35 eV, even more preferably less than 0.30 eV, or even less than 0.25 eV.

[0191] According to the invention, optoelectronic devices comprising at least one organic molecule according to the invention can be used, for example, as displays, light sources for lighting applications and as light sources for medical and / or cosmetic applications (e.g. phototherapy).

[0192] <Combination of organic molecules and additional substances according to the present invention> It forms part of general knowledge for a person skilled in the art that any layer within an optoelectronic device, here preferably an OLED, in particular the light-emitting layer (EML), may consist of a single material or a combination of different materials.

[0193] For example, those skilled in the art will understand that an EML is composed of a single material that emits light when a voltage (and current) is applied to the device. However, those skilled in the art will appreciate that in the EML of an optoelectronic device (here, preferably an OLED), different materials may be present, in particular one or more host materials (i.e., matrix materials; here, the host material H) may be present when included in an optoelectronic device comprising at least one organic molecule according to the present invention. B It will be appreciated that it is advantageous to combine a dopant material (referred to as an emitter material) with one or more dopant materials (ie, emitter materials), at least one of which emits light upon application of a voltage and current to the device.

[0194] In a preferred embodiment of the use of the organic molecules according to the invention in an optoelectronic device, said optoelectronic device comprises at least one organic molecule according to the invention in the EML, or in a layer directly adjacent to the EML, or in one or more of these layers.

[0195] In a preferred embodiment of the use of the organic molecules according to the invention in an optoelectronic device, said optoelectronic device is an OLED and comprises at least one organic molecule according to the invention in the EML, or in a layer directly adjacent to the EML, or in one or more of these layers.

[0196] In a more preferred embodiment of the use of the organic molecules according to the invention in an optoelectronic device, said optoelectronic device is an OLED and comprises at least one organic molecule according to the invention in an EML. The skilled person will understand that this means that at least one organic molecule according to the invention is, for example, in the host material H of the respective EML. B (i.e., a matrix material), or at least one host material H B It is understood that the term "optoelectronic device" means that the dopant (material) can be used as an emissive (i.e., an emitter material) or non-emissive (i.e., does not emit light when a voltage and current is applied to the optoelectronic device).

[0197] In one embodiment relating to an optoelectronic device, preferably an OLED, comprising at least one organic molecule according to the invention, at least one, preferably each organic molecule according to the invention is used as an emitter material in an emissive layer EML, i.e. it emits light when a voltage (and current) is applied across the device.

[0198] In another embodiment relating to an optoelectronic device, preferably an OLED, comprising at least one organic molecule according to the invention, at least one, preferably each, organic molecule according to the invention is present in the emissive layer EML but does not emit light when a voltage (and current) is applied to the device, i.e. the at least one organic molecule according to the invention is then in a host material H B or non-emissive dopants, both of which are known to those skilled in the art.

[0199] In one embodiment of an optoelectronic device, preferably an OLED, comprising at least one organic molecule according to the invention, the one or more organic molecules according to the invention are comprised in at least one EML. The skilled person will understand that this means that the one or more organic molecules according to the invention are either emitter materials (i.e. emissive dopant materials) in the EML or host materials H in the EML. B or both are non-emissive dopant materials in the EML, or the organic molecules are, independently of each other, a host material H B , is understood to mean selected from emitter materials (i.e., luminescent dopant materials) or non-luminescent dopant materials.

[0200] As known to those skilled in the art, for example, in an organic light emitting diode (OLED), emission from an emitter material (i.e., an emissive dopant) includes fluorescence from an excited singlet state (generally the lowest excited singlet state S1) and phosphorescence from an excited triplet state (generally the lowest excited triplet state T1).

[0201] Fluorescent emitter F can emit light at room temperature (i.e., (about) 20° C.) upon electronic excitation (e.g., in an optoelectronic device), and the emissive excited state is a singlet state. Fluorescent emitters generally exhibit immediate (i.e., direct) fluorescence on the nanosecond time scale when initial electronic excitation (e.g., by electron-hole recombination) provides an excited singlet state of the emitter.

[0202] In the context of the present invention, a delayed fluorescent material is a material that can reach an excited triplet state (generally the lowest excited triplet state T1) to an excited singlet state (generally the lowest excited singlet state S1) by reverse intersystem crossing (RISC; i.e., up-intersystem crossing or reverse intersystem crossing) and can emit light when returning from the excited singlet state (generally S1) thus reached to the electronic ground state. The time scale (generally in the microsecond range) at which the observed fluorescence emission occurs after RISC from an excited triplet state (generally T1) to an excited singlet state (generally S1) is slower than the time scale (generally in the nanosecond range) at which direct (i.e., immediate) fluorescence occurs, and is therefore referred to as delayed fluorescence (DF). When RISC from an excited triplet state (generally from T1) to an excited singlet state (generally to S1) occurs via thermal activation and the excited singlet state thus filled emits light (delayed fluorescence emission), the process is referred to as thermally activated delayed fluorescence (TADF). Therefore, a TADF material is a material that can emit thermally activated delayed fluorescence (TADF) as described above. The lowest excited singlet state energy level E(S1 E ) and the lowest excited triplet state energy level E(T1 E ) and the energy difference ΔE ST It is known to those skilled in the art that the switching from the lowest excited singlet state to the lowest excited triplet state by RISC occurs with high efficiency if ΔE ST It forms part of the general knowledge of the person skilled in the art that TADF materials have a value (see below). As known to the person skilled in the art, a TADF material is not simply a material capable of RISC on its own from an excited triplet state to an excited singlet state with subsequent release of TADF as described above. A TADF material is in fact a material that consists of two types of materials, preferably two host materials H B More preferably, the p-host material H P and n-host material H N It is known to those skilled in the art that the exciplex formed is (see below).

[0203] The (thermally activated) delayed fluorescence evolution is analyzed, for example, on the basis of decay curves obtained from time-resolved (i.e., transient) photoluminescence (PL) measurements. For this, spin-coated films of 1-10 wt. %, in particular 10 wt. %, of each emitter (i.e., the assumed TADF material) in poly(methyl methacrylate) (PMMA) are used as samples. The analysis is performed, for example, using an Edinburgh Instruments FS5 fluorescence spectrometer. A nitrogen atmosphere is maintained during measurements of the sample PMMA film in a cuvette. Data collection is performed using the well-established Time Correlated Single Photon Counting (TCSPC, see below) technique. Measurements can be performed and combined in four time domains (200 ns, 1 μs, 20 μs and even longer measurement periods of >80 μs) in order to collect the full decay dynamics over several orders of magnitude in time and signal intensity (see below).

[0204] TADF materials preferably meet the following two conditions in relation to the overall decay dynamics described above: (i) the damping dynamics exhibit two time domains, one in the nanosecond (ns) range and the other in the microsecond (μs) range; and (ii) The emission spectral morphology is consistent in the two time domains.

[0205] Here, the portion of the light emitted in the first decay region is considered to be immediate fluorescence, and the portion of the light emitted in the second decay region is considered to be delayed fluorescence.

[0206] The ratio of delayed to immediate fluorescence is expressed in the form of the so-called n-value, which is calculated by integrating the respective photoluminescence decays over time according to the following equation:

[0207] JPEG2025503881000034.jpg14170

[0208] In the context of the present invention, a TADF material preferably exhibits an n-value (ratio of delayed to immediate fluorescence) of greater than 0.05 (n>0.05), more preferably greater than 0.1 (n>0.1), even more preferably greater than 0.15 (n>0.15), particularly preferably greater than 0.2 (n>0.20) or even more preferably greater than 0.25 (n>0.25).

[0209] In a preferred embodiment, the organic molecules according to the invention exhibit an n value (ratio of delayed to immediate fluorescence) greater than 0.05 (n>0.05).

[0210] In the context of the present invention, the TADF material E B is the lowest excited singlet state energy level E(S1 E ) and the lowest excited triplet state energy level E(T1 E ) corresponds to the energy difference ΔE ST The TADF material E is characterized by exhibiting a value of less than 0.4 eV, preferably less than 0.3 eV, more preferably less than 0.2 eV, even more preferably less than 0.1 eV, or even less than 0.05 eV. B ΔE ST The method for determining the value is explained later in this text.

[0211] In a preferred embodiment, the organic molecule according to the present invention is a TADF material E as defined herein. B and ΔE corresponds to the energy difference between the lowest excited singlet state energy level and the lowest excited triplet state energy level. ST values ​​less than 0.4 eV, preferably less than 0.3 eV, more preferably less than 0.2 eV, even more preferably less than 0.13 eV, or even more preferably less than 0.07 eV.

[0212] In the paragraph on compositions comprising at least one organic molecule according to the invention (see below), one or more TADF substances E different from the organic molecule according to the invention may be BThe skilled artisan will recognize that any TADF material disclosed in the state of the art is a suitable TADF material in this context. B Those skilled in the art will also understand that the TADF material E B However, it is generally understood that the HOMO (Highest Occupied Molecular Orbital) and LUMO (Lowest Unoccupied Molecular Orbital) are designed to be largely spatially separated by the (electron) donor group and (electron) acceptor group, respectively. The groups are generally large in volume (i.e., sterically required) or are twisted by being linked via a spiro junction, reducing the spatial overlap of the HOMO and LUMO. However, minimizing the spatial overlap of the HOMO and LUMO has the disadvantage that the photoluminescence quantum yield (PLQY) of the TADF material is also reduced. Therefore, in practice, ΔE ST In order to reduce the load and achieve a high PLQY, both of these effects are taken into consideration.

[0213] One common approach for TADF material design is to covalently link one or more HOMO-distributed (electron) donor moieties and one or more LUMO-distributed (electron) acceptor moieties to the same bridge, referred to herein as a linker group. B may, for example, contain two or three linker groups attached to the same acceptor moiety, with additional donor and acceptor moieties attached to each of the two or three linker groups.

[0214] Also, one or more donor moieties and one or more acceptor moieties can be directly bonded to one another (without the presence of a linker group).

[0215] Typical donor moieties are derivatives of diphenylamine, indole, carbazole, acridine, phenoxazine and related structures. In particular, aliphatic, aromatic or heteroaromatic ring systems can be condensed to the aforementioned donor precursors to reach, for example, indolocarbazoles.

[0216] Derivatives of benzene, biphenyl, and to some extent terphenyl, are common linker groups.

[0217] Nitrile groups are very common acceptor moieties in TADF materials, well-known examples of which include:

[0218] (i) Carbazolyldicyanobenzene compounds 2CzPN (4,5-di(9H-carbazol-9-yl)phthalonitrile), DCzIPN (4,6-di(9H-carbazol-9-yl)isophthalonitrile), 4CzPN (3,4,5,6-tetra(9H-carbazol-9-yl)phthalonitrile), 4CzIPN (2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile), 4CzTPN (2,4,5,6-tetra(9H-carbazol-9-yl)terephthalonitrile) and their derivatives,

[0219] (ii) Carbazolylcyanopyridine compounds 4CzCNPy (2,3,5,6-tetra(9H-carbazol-9-yl)-4-cyanopyridine) and its derivatives,

[0220] (iii) Carbazolylcyanobiphenyl compounds CNBPCz (4,4',5,5'-tetra(9H-carbazol-9-yl)-[1,1'-biphenyl]-2,2'-dicarbonitrile), CzBPCN (4,4',6,6'-tetra(9H-carbazol-9-yl)-[1,1'-biphenyl]-3,3'-dicarbonitrile), DDCzIPN (3,3',5,5'-tetra(9H-carbazol-9-yl)-[1,1'-biphenyl]-2,2',6,6'-tetracarbonitrile) and their derivatives,

[0221] wherein in these materials one or more of the nitrile groups are substituted with fluorine (F) or trifluoromethyl (CF 3 ) may be substituted.

[0222] Nitrogen heterocycles such as triazine, pyrimidine, triazole, oxadiazole, thiadiazole, heptazine, 1,4-diazatriphenylene, benzothiazole, benzoxazole, quinoxaline, and diazafluorene derivatives are also well-known acceptor moieties used in TADF molecular constructions. For example, known examples of TADF molecules containing triazine acceptors include PIC-TRZ (7,7'-(6-([1,1'-biphenyl]-4-yl)-1,3,5-triazine-2,4-diyl)bis(5-phenyl-5,7-dihydroindolo[2,3-b]carbazole)), mBFCzTrz (5-(3-(4,6-diphenyl-1,3,5-triazin-2-yl))phenyl)-5H-benzofuro[3,2-c]carbazole), and DCzTrz (9,9'-(5-(4,6-diphenyl-1,3,5-triazin-2-yl)-1,3-phenylene)bis(9H-carbazole)).

[0223] Another group of TADF materials includes diaryl ketones such as benzophenone or (heteroaryl)aryl ketones such as 4-benzoylpyridine, 9,10-anthraquinone, 9H-xanthen-9-one and their derivatives as acceptor moieties to which donor moieties (mainly carbazolyl substituents) are attached. Examples of such TADF molecules include BPBCz (bis(4-(9'-phenyl-9H,9'H-[3,3'-bicarbazol]-9-yl)phenyl)methanone), mDCBP ((3,5-di(9H-carbazol-9-yl)phenyl)(pyridin-4-yl)methanone), AQ-DTBu-Cz (2,6-bis(4-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenyl)anthracene-9,10-dione), and MCz-XT (3-(1,3,6,8-tetramethyl-9H-carbazol-9-yl)-9H-xanthen-9-one), respectively.

[0224] Sulfoxides, particularly diphenyl sulfoxides, are also commonly used as acceptor moieties for the construction of TADF materials; well-known examples include 4-PC-DPS (9-phenyl-3-(4-(phenylsulfonyl)phenyl)-9H-carbazole), DitBu-DPS (9,9'-(sulfonylbis(4,1-phenylene))bis(9H-carbazole)), and TXO-PhCz (2-(9-phenyl-9H-carbazol-3-yl)-9H-thioxanthen-9-one 10,10-dioxide).

[0225] The fluorescent emitter F may also exhibit a TADF as defined herein, and more particularly a TADF material E as defined herein. B As a result, the small FWHM emitter S as defined herein is understood to be B is the TADF material E as defined herein B It may or may not be so.

[0226] Phosphorescence, i.e., emission from an excited triplet state (generally the lowest excited triplet state T1), is a spin-forbidden process. As known to those skilled in the art, phosphorescence can be enhanced by utilizing (intramolecular) spin-orbit interactions (the so-called (internal) heavy atom effect). In the context of the present invention, the phosphorescent material P B is a phosphorescent emitter capable of emitting phosphorescence at room temperature (i.e., (about) 20° C.).

[0227] Here, the phosphorescent material P B It is preferred that the phosphor P contains at least one atom of an element having a standard atomic weight greater than that of calcium (Ca). More preferably, in the context of the present invention, the phosphor P B contains transition metal atoms, particularly transition metal atoms of elements having a standard atomic weight greater than that of zinc (Zn). B The transition metal atoms preferably present in exist in any oxidation state (and can also exist as ions of the respective elements).

[0228] Phosphorescent material P used in optoelectronic devices B It is common knowledge for a person skilled in the art that the phosphorescent material P is Ir, Pd, Pt, Au, Os, Eu, Ru, Re, Ag and Cu, preferably Ir, Pt and Pd in ​​the context of the present invention, more preferably a complex of Ir and Pt. A person skilled in the art will understand what material is phosphorescent material P in optoelectronic devices. B Those skilled in the art are also familiar with the principles of designing phosphorescent complexes for use as phosphorescent materials in optoelectronic devices and know how to tune the emission of the complexes through structural changes.

[0229] Those skilled in the art will recognize that the phosphorescent material P used in optoelectronic devices B In this connection, the skilled person will be aware of which materials are suitable as the phosphorescent material P and how to synthesize them. B We are familiar with the principles of designing phosphorescent complexes for use as photocatalysts and know how to tune the emission of the complexes through structural changes.

[0230] Phosphorescent substances P that can be used with the organic molecules according to the invention B Non-limiting examples of (for example in the form of compositions or in the EML of optoelectronic devices, see below) are disclosed in the state of the art. For example, the following metal complexes can be used to produce phosphorescent materials P that can be used with the organic molecules according to the invention: B Is:

[0231] JPEG2025503881000035.jpg80170

[0232] In the context of the present invention, a small full width at half maximum (FWHM) emitter S B is any emitter (i.e., emitter material) having an emission spectrum exhibiting a FWHM of 0.35 eV or less (≦0.35 eV), preferably 0.30 eV or less (≦0.30 eV), in particular 0.25 eV or less (≦0.25 eV). Unless otherwise specified, this is determined with reference to the emission spectrum of each emitter at room temperature (i.e., (about) 20° C.), typically measured at 1-5 wt %, in particular 2 wt %, of the emitter in poly(methyl methacrylate) (PMMA). Alternatively, a small FWHM emitter S B The emission spectra of the emitters S are typically measured at room temperature (i.e., (approximately) 20 °C) in dichloromethane or toluene at 0.001–0.2 mg / mL. B can be measured in a solution.

[0233] Small FWHM emitter S B are fluorescent emitters F, phosphorescent emitters (e.g., phosphorescent materials P B ) and / or TADF emitters (e.g., TADF material E B The organic molecule according to the present invention, the aforementioned TADF material E B and phosphorescent material P B In the case of B or P B The thickness is measured from each spin-coated film.

[0234] As known to those skilled in the art, the emitter (e.g., a small FWHM emitter S B The full width at half maximum (FWHM) of the emission spectrum (fluorescence spectrum for fluorescent emitters and phosphorescence spectrum for phosphorescent emitters) is easily determined from the respective emission spectrum (fluorescence spectrum for fluorescent emitters and phosphorescence spectrum for phosphorescent emitters). All reported FWHM values ​​generally represent the main emission peak (i.e. the peak with the highest intensity). Means of determining the FWHM (here preferably reported in electron volts, eV) are part of the common knowledge of the skilled artisan. For example, if the main emission peak of an emission spectrum is determined by dividing the two wavelengths λ 2 , λ 3 , λ 4 , λ 5 , λ 6 , λ 7 , λ 8 , λ 9 , λ 10 , λ 11 , λ 12 , λ 13 , λ 14 , λ 15 , λ 20 , λ 25 , λ 30 , λ 40 , λ 50 , λ 16 , λ 20 , λ 30 , λ 40 , λ 50 , λ 17 , λ 20 , λ 25 , λ 30 , λ 20 , λ 30 , λ 40 , λ 5 ...30 , λ 40 , λ 50 , λ 30 , λ 1 and λ 2 When half the maximum emission (i.e., 50% of the maximum emission intensity) is reached at , the FWHM in electron volts (eV) is typically (and herein) determined using the following equation:

[0235] JPEG2025503881000036.jpg16170

[0236] In the context of the present invention, a small FWHM emitter S B is an organic emitter, which in the context of the present invention means that it does not contain any transition metal. Preferably, in the context of the present invention, a small FWHM emitter S B is composed primarily of the elements hydrogen (H), carbon (C), nitrogen (N) and boron (B), but can also contain, for example, oxygen (O), silicon (Si), fluorine (F) and bromine (Br).

[0237] Also, in the context of the present invention, a small FWHM emitter S B is preferably a fluorescent emitter F which may or may not additionally exhibit TADF.

[0238] Preferably, in the context of the present invention, a small FWHM emitter S B meets at least one of the following requirements: (i) Boron (B)-containing emitters, which have the respective small FWHM emitters S B means that at least one atom in is boron (B); (ii) contain a polycyclic aromatic or heteroaromatic core structure, where at least two aromatic rings are fused together (eg, anthracene, pyrene or aza derivatives thereof).

[0239] More preferably, in the context of the present invention, a small FWHM emitter S B meets at least one of the following requirements: (i) Boron (B)-containing emitters, which have the respective small FWHM emitters S B means that at least one atom in is boron (B); (ii) Contains a pyrene core structure.

[0240] Most preferably, in the context of the present invention, a small FWHM emitter S B are boron (B)-containing emitters, which are the small FWHM emitters S B This means that at least one atom in is boron (B).

[0241] Those skilled in the art will recognize that a small FWHM emitter S that meets the aforementioned requirements or preferred characteristics may be B Know how to design.

[0242] In the context of the present invention, a small FWHM emitter S B A class of fluorescent emitters F suitable as are the well-known 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) based materials, whose structural features and applications in optoelectronic devices have been discussed in detail and are common knowledge to those skilled in the art. The state of the art also shows how such materials can be synthesized and how to arrive at emitters with specific emission hues.

[0243] Those skilled in the art will also recognize that the BODIPY basic structure shown below is JPEG2025503881000037.jpg21170

[0244] For example, they are well aware of the fact that intermolecular π-π interactions and the associated self-quenching make them less than ideally suited as emitters in optoelectronic devices.

[0245] Alternative optoelectronic emitter materials have bulky (i.e. sterically demanding) groups as substituents attached to the BODIPY core structure described above. Such bulky groups can be, for example, aryl, heteroaryl, alkyl or alkoxy substituents (among many others) or fused polyaromatic or heteroaromatic groups, any of which can be optionally substituted. The selection of suitable substituents on the BODIPY core will be apparent to one skilled in the art and can be easily derived from the state of the art, as well as the numerous synthetic routes that have been established for the synthesis and subsequent modification of such molecules.

[0246] In the context of the present invention, a small FWHM emitter S B Examples of suitable BODIPY emitters are shown below:

[0247] JPEG2025503881000038.jpg74170

[0248] JPEG2025503881000039.jpg107170

[0249] JPEG2025503881000040.jpg84170

[0250] JPEG2025503881000041.jpg40170

[0251] In addition, one or both of the fluorine substituents bonded to the central boron atom of the BODIPY core structure may be bonded via an oxygen atom, preferably fluorine (F) or trifluoromethyl (CF 3It is known to those skilled in the art that emitters for optoelectronic devices can be arrived at by substituting alkoxy or aryloxy groups, optionally substituted with electron-withdrawing substituents such as aryloxy, ... B does not mean:

[0252] JPEG2025503881000042.jpg176170

[0253] Those skilled in the art will appreciate that virtually all BODIPY-based emitters and their derivatives used in the state of the art, e.g. as fluorescent emitters F, have a particularly small FWHM emitter S B It is understood that any of the above may be used with the organic molecules according to the present invention.

[0254] In the context of the present invention, a small FWHM emitter S B Another class of molecules suitable for providing a charge-transfer (Pt) emitter are near-range-charge-transfer (NRCT) emitters.

[0255] Typical NRCT emitters have been described in the literature as exhibiting a delayed component in the time-resolved photoluminescence spectrum, indicating short-range HOMO-LUMO separation.

[0256] A typical NRCT emitter exhibits only one emission band in the emission spectrum, whereas a typical fluorescent emitter exhibits multiple unique emission bands due to vibrational progression.

[0257] Those skilled in the art will appreciate that a small FWHM emitter S in the context of the present invention B Know how to design and synthesize suitable NRCT emitters.

[0258] A small FWHM emitter S as defined herein Band additional fluorescent emitters F (see below) that can be used with the organic molecules according to the invention are boron-containing emitters as shown below:

[0259] JPEG2025503881000043.jpg51170

[0260] JPEG2025503881000044.jpg55170

[0261] JPEG2025503881000045.jpg62170

[0262] JPEG2025503881000046.jpg58170

[0263] JPEG2025503881000047.jpg103170

[0264] JPEG2025503881000048.jpg53170

[0265] JPEG2025503881000049.jpg51170

[0266] JPEG2025503881000050.jpg49170

[0267] JPEG2025503881000051.jpg54170

[0268] Here, this means that only the materials shown are small FWHM emitters S in the context of the present invention. B It is not meant to be used as a

[0269] Small FWHM emitter S B Another group of fluorescent emitters F that can be used as small FWHM emitters S in the context of the present invention are boron-containing emitters that contain exactly one direct BN bond. B It is understood that the small FWHM emitter S BA non-limiting example is a boron-containing emitter containing exactly one direct BN bond, which includes or consists of the following structure:

[0270] JPEG2025503881000052.jpg42170

[0271] The structures may be further substituted, and the structural units and / or substituents may be linked to form fused ring systems.

[0272] Small FWHM emitter S B Specific non-limiting examples of emitters that can be used are:

[0273] JPEG2025503881000053.jpg226170

[0274] One approach to designing fluorescent emitters F relies on the use of fluorescent polycyclic aromatic or heteroaromatic core structures. The latter, in the context of the present invention, is any structure that comprises one or more aromatic or heteroaromatic rings, preferably two or more of said rings, which are more preferably fused to each other or linked via one or more direct bonds or linking atoms. That is, the fluorescent core structure comprises at least one, and preferably only one, rigid conjugated π-system.

[0275] The skilled person knows how to select a fluorescent core structure for a fluorescent emitter F. Non-limiting examples of common fluorescent core structures for fluorescent emitters F are as follows:

[0276] JPEG2025503881000054.jpg54170

[0277] JPEG2025503881000055.jpg45170

[0278] JPEG2025503881000056.jpg46170

[0279] JPEG2025503881000057.jpg53170

[0280] JPEG2025503881000058.jpg52170

[0281] JPEG2025503881000059.jpg31170

[0282] JPEG2025503881000060.jpg48170

[0283] JPEG2025503881000061.jpg56170

[0284] JPEG2025503881000062.jpg78170

[0285] In the present context, the term "fluorescent core structure" indicates that any molecule comprising said core can potentially be used as a fluorescent emitter F. The skilled person knows that the core structure of such a fluorescent emitter F may be optionally substituted and what substituents are suitable in connection therewith.

[0286] As known to those skilled in the art, the host material H of the EML B is a host material H that can transport electrons or positive charges through the EML. B Those skilled in the art will recognize that the host material H included in the EML of an optoelectronic device (e.g., an OLED) can transfer excitation energy to at least one emitter material doped in the EML. B Those skilled in the art will also appreciate that any host material H generally does not significantly contribute to the emission of light from the device when voltage and current are applied. B However, the p-host H P , n-host H showing high electron mobility N or a bipolar host material H that exhibits both high hole and high electron mobility BP I know for a fact that it is.

[0287] As known to those skilled in the art, the EML also contains at least one p-host H P and one n-host H N In particular, the EML comprises exactly one emitter material according to the invention and a n-host H N 2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine (T2T) as p-host H P The present invention also includes a mixed host system comprising a host selected from CBP, mCP, mCBP, 4,6-diphenyl-2-(3-(triphenylsilyl)phenyl)-1,3,5-triazine, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole, and 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole.

[0288] The EML contains at least one p-host H P and one n-host H N This includes so-called mixed host systems, where there are n-hosts H N contains groups derived from pyridine, pyrimidine, benzopyrimidine, 1,3,5-triazine, 1,2,4-triazine and 1,2,3-triazine, and the p-host H P includes radicals derived from indole, isoindole and preferably carbazole.

[0289] A person skilled in the art knows what materials are suitable host materials for use in optoelectronic devices. Any host material used in the state of the art is considered a suitable host material H in the context of the present invention. B It is understood that

[0290] In the context of the present invention, the p-host material H P Substance H B Non-limiting examples are listed below:

[0291] JPEG2025503881000063.jpg88170

[0292] JPEG2025503881000064.jpg104170

[0293] JPEG2025503881000065.jpg127170

[0294] JPEG2025503881000066.jpg79170

[0295] JPEG2025503881000067.jpg92170

[0296] JPEG2025503881000068.jpg54170

[0297] In the context of the present invention, the n-host material H N Substance H B Non-limiting examples are listed below:

[0298] JPEG2025503881000069.jpg98170

[0299] JPEG2025503881000070.jpg130170

[0300] JPEG2025503881000071.jpg48170

[0301] Those skilled in the art will appreciate that any material contained in the same layer, particularly the same EML, as well as materials in adjacent layers that are in close proximity at the interface between the adjacent layers, can come together to form an exciplex. Those skilled in the art will appreciate that exciplex-forming material pairs, particularly p-host H P and n-host H NThe present invention relates to a method for selecting a pair of materials, and selection criteria for the two components of the material pair, including HOMO and / or LUMO energy requirements. That is, when exciplex formation is required, one component, e.g., the p-host material H P The HOMO of the n-host material H N The HOMO of the host material H is at least 0.20 eV higher in energy than the HOMO of the host material H. P The LUMO of the n-host material H N The exciplex has an energy at least 0.20 eV higher than the LUMO of the exciplex of the present invention. It is common knowledge of a person skilled in the art that if an exciplex is present in the EML of an optoelectronic device, particularly an OLED, the exciplex has the function of an emitter material and can emit light when a voltage and a current are applied to the device. As is known from the state of the art and generally, an exciplex can be non-emissive and, for example, when it is included in the EML of an optoelectronic device, it can transfer excitation energy to an emitter material.

[0302] <Composition Comprising at Least One Organic Molecule According to the Present Invention> An aspect of the present invention relates to a composition comprising at least one organic molecule according to the present invention. An aspect of the present invention relates to the use of said composition in an optoelectronic device, preferably an OLED, in particular in the EML of said device.

[0303] Hereinafter, when describing the above compositions, the content of a specific substance in each composition may be referred to in the form of a percentage. It should be noted that unless otherwise specified in a specific embodiment, all percentages refer to weight percentages, which have the same meaning as weight percentages or weight % ((weight / weight), (w / w), wt%). For example, when the content of one or more organic molecules according to the present invention in a specific composition is illustratively referred to as 30%, this is understood to mean that the total weight of one or more organic molecules according to the present invention (i.e., all of those molecules combined) is 30% by weight, i.e., 30% of the total weight of the respective composition. By providing the preferred content of a component in weight%, it is understood that each time a composition is specified, the total content of all components adds up to 100% by weight (i.e., the total weight of the composition).

[0304] In the following description of embodiments of the present invention relating to compositions comprising at least one organic molecule according to the present invention, reference will be made to energy transfer processes occurring between components in said compositions when they are used in an optoelectronic device, preferably in the EML of an optoelectronic device, most preferably in the EML of an OLED. Those skilled in the art will understand that such excitation energy transfer processes can improve the luminous efficiency when the compositions are used in the EML of an optoelectronic device.

[0305] Those skilled in the art will understand that, for excitation energy transfer to occur (efficiently), there is preferably a spectral overlap between the emission spectrum of the energy donor and the absorption spectrum of the energy acceptor. Also, those skilled in the art will understand that the intended energy donor must have a higher excited state energy level than the intended energy acceptor, i.e., the energy level E(S1)(donor) of the lowest excited singlet state S1(donor) of the energy donor and / or the energy level E(T1)(donor) of the lowest excited triplet state T1(donor) of the energy donor is preferably higher in energy than the energy level E(S1)(acceptor) of the lowest excited singlet state S1(acceptor) of the energy acceptor and / or the energy level E(T1)(acceptor) of the lowest excited triplet state T1(acceptor) of the energy acceptor. The selection of a substance that satisfies the above-mentioned preferred criteria can be easily achieved based on the standard knowledge of those skilled in the art without the inventive step. Experimental details on how to determine excited state energies and how to record absorption and emission spectra are provided in later sections of the text.

[0306] When describing a composition comprising at least one organic molecule according to the present invention, it will also be noted that certain substances are "different" from other substances, meaning that substances that are "different" from one another do not have identical chemical structures.

[0307] In one embodiment, the composition comprises, or alternatively consists of: (a) one or more organic molecules according to the present invention; (b) one or more host materials H, optionally different from the organic molecules of (a); B , (c) one or more TADF substances E, optionally different from the organic molecules of (a); B , (d) optionally one or more phosphorescent substances P different from the organic molecules of (a); B , (e) optionally different from the organic molecule of (a) and a TADF material E of (c); Bone or more fluorescent emitters F different from (f) optionally one or more solvents and / or dyes;

[0308] wherein any of (a) to (e) substances (substances of the same group as defined above and / or substances of different groups as defined above) optionally form one or more exciplexes; wherein at least one of the substances (a) and / or (c) and / or (d), and / or at least one exciplex, is an emitter substance if the fluorescent emitter F of (e) is absent from the composition.

[0309] at least one organic molecule according to the invention and (optionally) at least one host substance H B A composition comprising: One embodiment of the composition according to the invention comprises at least one organic molecule according to the invention and, optionally, at least one host material H structurally different from the molecule of the invention. B The present invention relates to a composition comprising:

[0310] Preferably, at least one, and preferably each, emitter material of said compositions emits light with a maximum emission between 500 and 560 nm, more preferably between 510 and 550 nm, and even more preferably between 520 and 540 nm, in an emission spectrum measured from a spin-coated film of 10% by weight of each emitter in poly(methyl methacrylate) (PMMA) at room temperature (i.e. (about) 20° C.). When present, at least one, and preferably each, host material H B is at least one, preferably the lowest excited singlet state S1 (H B When present, at least one, and preferably each, host material H Bis preferably capable of transferring excitation energy to at least one, preferably each, emitter substance. The excitation energy can also be transferred between different organic molecules according to the invention, where it is particularly preferred that the excitation energy is transferred to at least one, preferably each, emitter substance.

[0311] In one embodiment, the composition comprises, or alternatively consists of: (a) one or more organic molecules according to the present invention; (b) one or more host substances H different from the organic molecules of (a) B , and (c) optionally one or more solvents.

[0312] In one embodiment, the composition comprises, or alternatively consists of: (a) one or more organic molecules according to the present invention, and (b) one or more host substances H different from the organic molecules of (a) B , Here, the host material H in the composition B is higher than the fraction (wt. %) of the organic molecules according to the invention, and preferably the fraction (wt. %) of the host material H in the composition B is twice as high as the fraction (% by weight) of the organic molecules according to the invention.

[0313] In one embodiment, the composition comprises, or alternatively consists of: (a) 1 to 50% by weight, preferably 5 to 40% by weight, in particular 10 to 30% by weight, of one or more organic molecules according to the invention, (b) 5 to 99% by weight, preferably 30 to 95% by weight, in particular 40 to 90% by weight, of one or more host substances H different from the organic molecules of (a). B , and (c) 0 to 94% by weight, preferably 0 to 65% by weight, in particular 0 to 50% by weight, of one or more solvents, wherein, in certain embodiments, the total weight of materials from groups (a) to (c) is 100% by weight.

[0314] Compositions Comprising at Least One Organic Molecule According to the Invention Together with at Least One (Additional) Fluorescent Emitter F A preferred embodiment of said composition concerns a composition comprising at least one organic molecule according to the invention and at least one fluorescent emitter F (as defined above) which is not a molecule of the invention (i.e. if the organic molecule according to the invention is the fluorescent emitter, an additional fluorescent emitter F can be present in the composition).

[0315] In this case, any organic molecule according to the invention and at least one (additional) fluorescent emitter F can play the role of an emitter material, but preferably, when used in the EML of an optoelectronic device, the emission from the composition is mainly (i.e. at least 50%, preferably at least 60%, more preferably at least 70%, even more preferably at least 80% or even more preferably at least 90%) attributable to at least one, preferably exactly one, (additional) fluorescent emitter F, which is structurally different from the molecule of the invention. Furthermore, the excitation energy is preferably shared between different substances in the composition, in particular at least one, preferably the respective host substance H B At least one, preferably each, TADF material E B and to at least one, preferably each (additional) fluorescent emitter F. The excitation energy is also preferably transferred between substances in the composition selected from: at least one organic molecule according to the invention and at least one (additional) fluorescent emitter F, in particular from at least one, preferably each organic molecule according to the invention to at least one, preferably each (additional) fluorescent emitter F. The at least one, preferably each (additional) fluorescent emitter F is dissolved in 1-5 wt. % of each S, preferably 2 wt. % of each S in poly(methyl methacrylate) (PMMA) at room temperature (i.e. (approximately) 20° C.). BIn the context of the present invention, a small FWHM emitter S emits green light with a maximum emission of preferably 500 to 560 nm, more preferably 510 to 550 nm, and even more preferably 520 to 540 nm in the emission spectrum measured from a spin-coated film of B It is particularly preferred that:

[0316] In one embodiment, the composition comprises, or alternatively consists of: (a) one or more organic molecules according to the present invention; (b) one or more host materials H, optionally different from the organic molecules of (a); B , (c) one or more fluorescent emitters F different from the organic molecules of (a), and (d) optionally one or more solvents;

[0317] wherein at least one, preferably each, fluorescent emitter F of group (c) is present at room temperature (i.e. (approximately) 20° C.) in poly(methyl methacrylate) (PMMA) at 1-5 wt. %, preferably 2 wt. %, of each S B In the context of the present invention, a small FWHM emitter S emits green light with a maximum emission of preferably 500 to 560 nm, more preferably 510 to 550 nm, and even more preferably 520 to 540 nm in the emission spectrum measured from a spin-coated film of B It is preferable that:

[0318] In one embodiment, the composition comprises, or alternatively consists of: (a) one or more organic molecules according to the present invention, and (c) one or more fluorescent emitters F different from the organic molecules of (a); Here, the fraction (wt %) of the organic molecules of group (a) is higher than the fraction (wt %) of the fluorescent emitter F of group (c), preferably the fraction (wt %) of the organic molecules of group (a) is at least 5 times higher than the fraction (wt %) of the fluorescent emitter F of group (c).

[0319] In one embodiment, the composition comprises, or alternatively consists of: (a) 1 to 50% by weight, preferably 5 to 40% by weight, in particular 10 to 30% by weight, of one or more organic molecules according to the invention, (b) 30 to 98.9% by weight, preferably 48 to 94.5% by weight, in particular 65 to 89% by weight, of one or more host substances H different from the organic molecules of (a). B , (c) 0.1 to 20% by weight, preferably 0.5 to 12% by weight, in particular 1 to 5% by weight, of one or more (additional) fluorescent emitters F different from the organic molecules of (a), and (d) optionally 0 to 68.9% by weight, preferably 0 to 46.5% by weight, in particular 0 to 24% by weight, of one or more solvents,

[0320] wherein at least one, preferably each, fluorescent emitter F of (c) is present at room temperature (i.e. (about) 20° C.) in poly(methyl methacrylate) (PMMA) at 1-5 wt %, preferably 2 wt %, of each S B In the context of the present invention, a small FWHM emitter S emits green light with a maximum emission of preferably 500 to 560 nm, more preferably 510 to 550 nm, and even more preferably 520 to 540 nm in the emission spectrum measured from a spin-coated film of B It is preferred that wherein, in certain embodiments, the total weight of materials from groups (a) to (d) is 100% by weight.

[0321] <At least one (additional) TADF substance E B and at least one organic molecule according to the present invention. Another preferred embodiment of the composition is a composition comprising at least one organic molecule according to the invention and at least one TADF material E which is not a molecule of the invention, i.e. structurally different. B (as defined above).

[0322] In this case, at least one organic molecule according to the invention and at least one TADF substance E B Any material selected from the group can act as an emitter material. Furthermore, the excitation energy can be transmitted between different materials in the composition, in particular between at least one, and preferably each, of the host materials H B From at least one, preferably each TADF material E B and / or to at least one, preferably each, organic molecule according to the invention. The excitation energy is also transferred to at least one organic molecule according to the invention and to at least one TADF material E B In particular, it is preferable that the at least one, preferably each emitter material is transferred between the materials in the composition selected from at least one organic molecule according to the invention and at least one TADF material E B It is particularly preferred that at least one, and preferably each, substance selected from the group consisting of, acting as an emitter substance, emits green light, preferably with an emission maximum of 500 to 560 nm, more preferably 510 to 550 nm, even more preferably 520 to 540 nm, in an emission spectrum measured at room temperature (i.e. (about) 20° C.) from a spin-coated film of 10 wt. % of each emitter in poly(methyl methacrylate) (PMMA).

[0323] In one embodiment, the composition comprises, or alternatively consists of: (a) one or more organic molecules according to the present invention; (b) one or more host materials H, optionally different from the organic molecules of (a); B , (c) one or more TADF substances E different from the organic molecules of (a); B , and (d) optionally one or more solvents.

[0324] In one embodiment, the composition comprises, or alternatively consists of: (a) one or more organic molecules according to the present invention, and (c) one or more TADF substances E different from the organic molecules of (a); B ,

[0325] Here, TADF material E of group (c) B The fraction (wt%) of the organic molecules of group (a) is higher than the fraction (wt%) of the TADF material E of group (c). B is at least two times higher than the fraction (wt. %) of the organic molecules of group (a).

[0326] In one embodiment, the composition comprises, or alternatively consists of: (a) 1 to 50% by weight, preferably 5 to 40% by weight, in particular 10 to 30% by weight, of one or more organic molecules according to the invention, (b) 0 to 98.9% by weight, preferably 20 to 94.5% by weight, in particular 40 to 89% by weight, of one or more host substances H different from the organic molecules of (a). B , (c) 0.1 to 50% by weight, preferably 0.5 to 40% by weight, in particular 1 to 30% by weight of one or more TADF substances E different from the organic molecules of (a) B , and (d) 0 to 98.9% by weight, preferably 20 to 74.5% by weight, in particular 30 to 49% by weight, of one or more solvents,

[0327] wherein at least one of (a) and / or (c) is an emitter material; wherein, in certain embodiments, the total weight of materials from groups (a) to (c) is 100% by weight.

[0328] <At least one (additional) TADF substance E B and a composition comprising at least one organic molecule according to the invention together with at least one (additional) fluorescent emitter F. Yet another preferred embodiment of the composition is one or more organic molecules according to the present invention, one or more TADF substances E which are not organic molecules according to the present invention. B(as defined above) and one or more (additional) fluorescent emitters F (as defined above) which are not molecules of the invention.

[0329] In this case, at least one organic molecule according to the invention, at least one (additional) TADF substance E B Any material selected from and at least one (additional) fluorescent emitter F can perform the role of an emitter material. However, preferably, when used in an EML of an optoelectronic device, the emission from the composition is mainly (i.e., more than 50%, preferably more than 60%, more preferably more than 70%, even more preferably more than 80%, or even more than 90%) attributable to at least one, preferably exactly one (additional) fluorescent emitter F which is not a molecule of the invention. At least one, preferably each (additional) fluorescent emitter F is dissolved in a solvent at room temperature (i.e., (about) 20° C.) in a concentration of 1-5% by weight, preferably 2% by weight, of each S in poly(methyl methacrylate) (PMMA). B In the context of the present invention, a small FWHM emitter S emits green light with a maximum emission of preferably 500 to 560 nm, more preferably 510 to 550 nm, and even more preferably 520 to 540 nm in the emission spectrum measured from a spin-coated film of B It is particularly preferred that the excitation energy is preferably different between the different substances in the composition, in particular between at least one, preferably each, of the host substances H B At least one, preferably each, TADF material E B and to at least one, preferably each, (additional) fluorescent emitter F. The excitation energy can preferably also be transferred between substances within the composition selected from: at least one organic molecule according to the invention, at least one (additional) TADF substance E B and at least one (additional) fluorescent emitter F, In particular, at least one, preferably each, organic molecule according to the invention and / or at least one, preferably each, (additional) TADF substance E B from, It is preferred that the fluorescence intensity can be transmitted to at least one, preferably each, (additional) fluorescent emitter F.

[0330] In one embodiment, the composition comprises, or alternatively consists of: (a) one or more organic molecules according to the present invention; (b) one or more host materials H, optionally different from the organic molecules of (a); B , (c) one or more (additional) TADF substances E different from the organic molecules of (a); B , (d) A TADF material E that is different from the organic molecule in (a) and is also different from the organic molecule in (c). B one or more (additional) fluorescent emitters F different from (e) optionally one or more solvents;

[0331] wherein at least one, preferably each, fluorescent emitter F of (d) is present at room temperature (i.e. (about) 20° C.) in poly(methyl methacrylate) (PMMA) at a concentration of 1-5 wt %, preferably 2 wt %, of each S B In the context of the present invention, a small FWHM emitter S emits green light having a maximum emission preferably between 500 and 560 nm, more preferably between 510 and 550 nm, and even more preferably between 520 and 540 nm in the emission spectrum measured from a spin-coated film of B It is preferable that:

[0332] In one embodiment, the composition comprises, or alternatively consists of: (a) one or more organic molecules according to the present invention; (c) one or more TADF substances E different from the organic molecules of (a); B , and (d) A TADF material E that is different from the organic molecule in (a) and is also different from the organic molecule in (c). Bone or more fluorescent emitters F distinct from

[0333] Here, TADF material E of group (c) B The fraction (wt%) of the organic molecules of group (a) is higher than the fraction (wt%) of the TADF material E of group (c). B is at least two times higher than the fraction (wt. %) of the organic molecules of group (a); Here, the fraction (wt %) of the organic molecules of group (a) is higher than the fraction (wt %) of the fluorescent emitter F of group (d), and preferably, the fraction (wt %) of the organic molecules of group (a) is at least two times higher than the fraction (wt %) of the fluorescent emitter F of group (d).

[0334] In one embodiment, the composition comprises, or alternatively consists of: (a) 1 to 50% by weight, preferably 5 to 40% by weight, in particular 10 to 30% by weight, of one or more organic molecules according to the invention, (b) 0 to 98.8% by weight, preferably 0 to 94% by weight, in particular 0 to 88% by weight, of one or more host substances H different from the organic molecules of (a). B , (c) 0.1 to 98.9% by weight, preferably 0.5 to 94.5% by weight, in particular 1 to 89% by weight, of one or more TADF substances E different from the organic molecules of (a). B , (d) 0.1 to 20% by weight, preferably 0.5 to 12% by weight, in particular 1 to 5% by weight of a TADF material E different from the organic molecules of (a) and of (c). B one or more (additional) fluorescent emitters F different from (e) 0 to 98.8% by weight, preferably 0 to 94% by weight, in particular 0 to 88% by weight, of one or more solvents,

[0335] wherein at least one, preferably each (additional) fluorescent emitter F (i.e., substance (d)) is present at room temperature (i.e., (about) 20° C.) in poly(methyl methacrylate) (PMMA) at a concentration of 1-5 wt. %, preferably 2 wt. %, of each S BIn the context of the present invention, a small FWHM emitter S emits green light with a maximum emission of preferably 500 to 560 nm, more preferably 510 to 550 nm, and even more preferably 520 to 540 nm in the emission spectrum measured from a spin-coated film of B It is preferred that wherein, in certain embodiments, the total weight of materials from groups (a) through (e) is 100% by weight.

[0336] At least one phosphorescent material P B and at least one organic molecule according to the present invention. Yet another preferred embodiment of the composition comprises at least one organic molecule according to the invention and at least one phosphorescent material P which is not a molecule according to the invention. B (as defined above).

[0337] In this case, at least one organic molecule according to the invention and at least one phosphorescent substance P B Any material selected from the group can act as the emitter material.

[0338] When used in an EML of an optoelectronic device, the emission from the composition is predominantly (i.e., 50% or more, preferably 60% or more, more preferably 70% or more, even more preferably 80% or more, or even 90% or more) due to at least one phosphorescent material P. B at least one, preferably each, of the organic molecules according to the invention has a lowest excited singlet state S1 attributable to at least one, preferably each, of the phosphorescent material P B It is preferred that the lowest excited triplet state T1 of the phosphorescent material P is energetically higher than that of the lowest excited triplet state T2 of the phosphorescent material P. Then, at least one, preferably each, organic molecule according to the present invention is B It is preferable to transfer the excitation energy to

[0339] When used in an EML of an optoelectronic device, if the emission from said composition is primarily (i.e., 50% or more, preferably 60% or more, more preferably 70% or more, even more preferably 80% or more, or even more than 90%) attributable to at least one organic molecule according to the present invention, then at least one, preferably each, phosphorescent material P B is energetically higher than the lowest excited triplet state T1 of at least one, preferably each, of the organic molecule according to the invention. B Preferably, the organic molecule according to the present invention is a TADF material E as defined herein. B In this case, it is generally preferred that in the composition at least one, preferably each phosphorescent material P B At least one, preferably each, TADF substance E contained in the composition is activated by an external heavy atom effect, which forms part of the common knowledge of the person skilled in the art. B Within this, the efficiency of the RISC process can be improved.

[0340] In one embodiment, the composition comprises, or alternatively consists of: (a) one or more organic molecules according to the present invention; (b) one or more host materials H, optionally different from the organic molecules of (a); B , (c) one or more phosphorescent substances P different from the organic molecules of (a) B , and (d) optionally one or more solvents; Here, at least one of the materials (a) and / or (c) is an emitter material.

[0341] In one embodiment, the composition comprises, or alternatively consists of: (a) one or more organic molecules according to the present invention, and (c) one or more phosphorescent substances P different from the organic molecules of (a) B ,

[0342] Here, the fraction (wt%) of the organic molecules of group (a) is the phosphorescent material P of group (c). B and preferably the fraction (wt%) of the organic molecules of group (a) is higher than the fraction (wt%) of the phosphorescent material P of group (c). B is at least two times higher than the fraction (wt%) of

[0343] In one embodiment, the composition comprises, or alternatively consists of: (a) 1 to 99.5% by weight, preferably 5 to 50% by weight, in particular 10 to 30% by weight, of one or more organic molecules according to the invention, (b) 0 to 98.5% by weight, preferably 35 to 94% by weight, in particular 60 to 88% by weight, of one or more host substances H different from the organic molecules of (a). B , (c) 0.5 to 20% by weight, preferably 1 to 15% by weight, in particular 2 to 10% by weight, of one or more phosphorescent substances P different from the organic molecules of (a). B , and (d) 0 to 98.5% by weight, preferably 0 to 59% by weight, in particular 0 to 28% by weight, of one or more solvents,

[0344] wherein at least one of (a) and / or (c) is an emitter material; wherein, in certain embodiments, the total weight of materials from groups (a) to (d) is 100% by weight.

[0345] At least one phosphorescent material P B and a composition comprising at least one organic molecule according to the invention together with at least one (additional) fluorescent emitter F. Yet another preferred embodiment of the composition comprises at least one organic molecule according to the invention and at least one phosphorescent substance P which is not a molecule according to the invention. B(as defined above) and at least one (additional) fluorescent emitter F (as defined above) which is not a molecule of the invention.

[0346] In this case, at least one organic molecule according to the invention, at least one phosphorescent substance P B Any material selected from and the at least one (additional) fluorescent emitter F can perform the role of an emitter material. However, preferably, when used in an EML of an optoelectronic device, the emission from the composition is mainly (i.e. more than 50%, preferably more than 60%, more preferably more than 70%, even more preferably more than 80% or even more than 90%) attributable to at least one, preferably exactly one (additional) fluorescent emitter F which is not a molecule of the invention. The at least one, preferably each (additional) fluorescent emitter F is dissolved in a solvent at room temperature (i.e. (about) 20° C.) of 1-5% by weight, preferably 2% by weight, of each S in poly(methyl methacrylate) (PMMA). B In the context of the present invention, a small FWHM emitter S emits green light having a maximum emission preferably between 500 and 560 nm, more preferably between 510 and 550 nm, and even more preferably between 520 and 540 nm in the emission spectrum measured from a spin-coated film of B Furthermore, the excitation energy is preferably uniform between the different substances in the composition, in particular between at least one, and preferably each, of the host substances H B from at least one, preferably each, organic molecule according to the invention, at least one, preferably each, phosphorescent substance P B , and to at least one, preferably each, (additional) fluorescent emitter F. The excitation energy is also preferably transferred between substances in the composition selected from: at least one organic molecule according to the invention, at least one phosphorescent material P B and at least one (additional) fluorescent emitter F, In particular, at least one, preferably each, organic molecule according to the invention and / or at least one, preferably each, phosphorescent material P B to at least one, preferably each (additional) fluorescent emitter F. Preferably, the excitation energy is transmitted from at least one, preferably each, organic molecule according to the invention to at least one, preferably each, phosphorescent material P B It can also be transmitted to

[0347] In one embodiment, the composition comprises, or alternatively consists of: (a) one or more organic molecules according to the present invention; (b) one or more host materials H, optionally different from the organic molecules of (a); B , (c) one or more phosphorescent substances P different from the organic molecules of (a) B , (d) A phosphorescent material P that is different from the organic molecule in (a) and is B one or more fluorescent emitters F different from (e) optionally one or more solvents;

[0348] wherein at least one, preferably each (additional) fluorescent emitter F (i.e., substance (d)) is present at room temperature (i.e., (about) 20° C.) in poly(methyl methacrylate) (PMMA) at a concentration of 1-5 wt. %, preferably 2 wt. %, of each S B In the context of the present invention, a small FWHM emitter S emits green light having a maximum emission preferably between 500 and 560 nm, more preferably between 510 and 550 nm, and even more preferably between 520 and 540 nm in the emission spectrum measured from a spin-coated film of B It is preferable that:

[0349] In one embodiment, the composition comprises, or alternatively consists of: (a) one or more organic molecules according to the present invention; (c) one or more phosphorescent substances P different from the organic molecules of (a) B , and (d) A phosphorescent material P that is different from the organic molecule in (a) and is B one or more fluorescent emitters F distinct from

[0350] Here, the fraction (wt%) of the organic molecules of group (a) is the phosphorescent material P of group (c). B and preferably the fraction (wt%) of the organic molecules of group (a) is higher than the fraction (wt%) of the phosphorescent material P of group (c). B at least twice as high as the fraction (wt%) of Here, the fraction (wt %) of the organic molecules of group (a) is higher than the fraction (wt %) of the fluorescent emitter F of group (d), preferably the fraction (wt %) of the organic molecules of group (a) is at least 5 times higher than the fraction (wt %) of the fluorescent emitter F of group (d).

[0351] In one embodiment, the composition comprises, or alternatively consists of: (a) 1 to 99.8% by weight, preferably 5 to 50% by weight, in particular 10 to 30% by weight, of one or more organic molecules according to the invention, (b) 0 to 98.8% by weight, preferably 35 to 94% by weight, in particular 60 to 88% by weight, of one or more host substances H different from the organic molecules according to the invention. B , (c) 0.1 to 20% by weight, preferably 0.5 to 10% by weight, in particular 1 to 3% by weight, of one or more phosphorescent substances P different from the organic molecules of (a). B , (d) 0.1 to 20% by weight, preferably 0.5 to 12% by weight, in particular 1 to 5% by weight, of one or more (additional) fluorescent emitters F different from the organic molecules of (a), and (e) 0 to 98.8% by weight, preferably 0 to 59% by weight, in particular 0 to 28% by weight, of one or more solvents,

[0352] wherein at least one, preferably each (additional) fluorescent emitter F (i.e., substance (d)) is present at room temperature (i.e., (about) 20° C.) in poly(methyl methacrylate) (PMMA) at a concentration of 1-5 wt. %, preferably 2 wt. %, of each S B In the context of the present invention, a small FWHM emitter S emits green light having a maximum emission preferably between 500 and 560 nm, more preferably between 510 and 550 nm, and even more preferably between 520 and 540 nm in the emission spectrum measured from a spin-coated film of B It is preferred that wherein, in certain embodiments, the total weight of materials from groups (a) through (e) is 100% by weight.

[0353] Further aspects and embodiments of the present invention In a preferred embodiment, the organic molecules according to the invention have a photoluminescence quantum yield (PLQY) of 20% or more, more preferably 30% or more, even more preferably 40% or more, particularly 50% or more, particularly 60% or more, especially 70% or more, or even more preferably 80% or more, where the PLQY of the organic molecules according to the invention is determined from a spin-coated film having 10 wt. % of the organic molecules in poly(methyl methacrylate) (PMMA) at room temperature (i.e. (about) 20° C.) as described in the section later in the text.

[0354] In one embodiment of the invention, the organic molecules according to the invention have a delayed excited state lifetime of 50 μs or less, preferably 25 μs or less, more preferably 15 μs or less, even more preferably 10 μs or less, particularly 8 μs or less, especially 6 μs or less, and especially preferably 4 μs or less, when measured at room temperature (i.e. (about) 20° C.) in a poly(methyl methacrylate) (PMMA) film having 10% by weight of the organic molecules.

[0355] In a further embodiment, the organic molecules according to the present invention have a full width at half maximum (FWHM) of less than 0.60 eV, preferably less than 0.50 eV, more preferably less than 0.45 eV, even more preferably less than 0.43 eV, or even more preferably less than 0.40 eV in a poly(methyl methacrylate) (PMMA) film having 10% by weight of the organic molecules at room temperature (i.e. (about) 20° C.).

[0356] In a further embodiment, the organic molecules according to the invention have a delayed excited state lifetime of 50 μs or less, preferably 25 μs or less, more preferably 15 μs or less, even more preferably 10 μs or less, particularly 8 μs or less, in particular 6 μs or less, and especially preferably 4 μs or less, in a poly(methyl methacrylate) (PMMA) film having 10 wt. % of the organic molecules at room temperature (i.e. (about) 20° C.), and a full width at half maximum (FWHM) of less than 0.60 eV, preferably less than 0.50 eV, more preferably less than 0.45 eV, even more preferably less than 0.43 eV, or even less than 0.40 eV.

[0357] In a further embodiment of the present invention, the organic molecules according to the present invention have an emission peak in the visible or near UV range, i.e. in the wavelength range of 380 to 800 nm, with a full width at half maximum (FWHM) of less than 0.60 eV, preferably less than 0.50 eV, more preferably less than 0.45 eV, even more preferably less than 0.43 eV, or even more preferably less than 0.40 eV, when measured in a poly(methyl methacrylate) (PMMA) film with 10% by weight of the organic molecules at room temperature (i.e. (about) 20° C.).

[0358] A further aspect of the present invention relates to a method for producing an optoelectronic component or device, preferably an optoelectronic device, comprising one or more organic molecules according to the present invention.

[0359] A further aspect of the present invention relates to a method for producing an optoelectronic device in which an organic molecule according to the present invention or a composition comprising an organic molecule according to the present invention is used.

[0360] Optoelectronic devices, in particular OLEDs, comprising at least one molecule according to the invention may be produced by any means of gas phase deposition and / or liquid processes.

[0361] Known methods for forming the individual layers of an OLED include: - Deposition by sublimation process, - Deposition by organic vapor phase deposition process; - Deposition by carrier gas sublimation process, -Solution processed or printed.

[0362] A further aspect of the invention relates to a method for manufacturing an optoelectronic device, in which an organic molecule according to the invention or a composition comprising an organic molecule according to the invention is used, in particular comprising the step of processing the organic molecule using a vacuum deposition method or from a solution.

[0363] The methods used to manufacture optoelectronic devices, preferably optoelectronic devices such as OLEDs, comprising at least one organic molecule according to the invention are known to those skilled in the art. The different layers are deposited individually and successively on a suitable substrate by subsequent deposition steps. The individual layers can be deposited using the same or different deposition methods.

[0364] The vapor deposition processes include thermal (co)evaporation, chemical vapor deposition, and physical vapor deposition. For active matrix OLED displays, an AMOLED backplane is used as the substrate. The individual layers are also processed from solutions or dispersions using appropriate solvents. For example, solution deposition processes include spin coating, dip coating, and jet printing. Solution processing is optionally performed in an inert atmosphere (e.g., nitrogen atmosphere), and the solvent is optionally completely or partially removed by means known in the art.

[0365] Preferably, the optoelectronic device comprising at least one organic molecule according to the invention has one or more layers in which the material is 10 -5They are characterized by the OVPD (Organic Vapor Phase Deposition) process applied at pressures between mbar and 1 bar or by coating with the aid of carrier gas sublimation. A special case of this process is the OVJP (Organic Vapor Jet Printing) process, in which the substance is applied directly via a nozzle and structured.

[0366] Also preferably, the optoelectronic element comprising at least one organic molecule according to the invention is characterized in that one or more layers are produced from solution, for example by spin-coating or by any desired printing process, for example by screen printing, flexographic printing, nozzle printing or offset printing, but particularly preferably by LITI (Light Induced Thermal Imaging, Thermal Transfer Printing) or inkjet printing.For this, soluble compounds are required.High solubility can be achieved through appropriate substitution of the compounds.

[0367] For example, a hybrid process is also possible in which one or more layers are applied from solution and one or more additional layers are applied by vapor phase deposition. Thus, for example, an emissive layer can be applied from solution and an electron transport layer can be applied by vapor deposition.

[0368] Those processes / methods are generally known to the person skilled in the art and are applicable without any inventive step to optoelectronic devices comprising at least one molecule according to the invention.

[0369] In a further aspect, the present invention relates to a method for generating light, in particular for generating green light of wavelength between 500 and 560 nm, comprising the steps of: (i) providing an optoelectronic device comprising an organic molecule according to the invention; and (ii) applying a current to the element.

[0370] The core element of a light-generating optoelectronic device is typically at least one light-emitting layer (EML) located between a positive electrode and a negative electrode. When a voltage (and current) is applied to the positive and negative electrodes of the optoelectronic device, holes and electrons are injected from the positive and negative electrodes, respectively. A hole-transporting layer (HTL) is typically located between the light-emitting layer (EML) and the positive electrode, and an electron-transporting layer (ETL) is typically located between the light-emitting layer (EML) and the negative electrode. The different layers are arranged in sequence. Recombination of holes and electrons in the EML then generates high-energy excitons. Decay of such excited states (e.g., singlet states such as S1 and / or triplet states such as T1) to the bottom state S0 preferably causes light emission.

[0371] <Orbital energies, excited state energies and ΔE ST Decision > The orbital energies and excited state energies are determined via experimental and quantum chemical methods, in particular computational methods using density functional theory calculations. The highest occupied molecular orbital energy E HOMO is determined from cyclic voltammetry measurements with an accuracy of 0.1 eV by methods known to those skilled in the art.

[0372] Lowest unoccupied orbital energy E LUMO is determined from cyclic voltammetry measurements with an accuracy of 0.1 eV by methods known to those skilled in the art. LUMO If is determined by cyclic voltmeter measurements, Alternatively, and preferably, E LUMO E HOMO +E gap where E gap is determined from the onset of the photoluminescence (PL) spectrum (normal state spectrum) measured from a spin-coated film of the respective material, typically poly(methyl methacrylate) (PMMA), at room temperature (i.e. (approximately) 20° C.). For the organic molecules according to the invention, typically the TADF material E B In the case of phosphorescent material P BIn the case of the TADF material E, the concentration of the respective material in the spin-coated PMMA film is 10 wt %, unless otherwise stated. B Not a host material H B On the other hand, the PL spectrum is generally B In the case of fluorescent emitters F which are different from the molecules of the present invention (i.e. are not represented by the general formula X), in particular, they are considered to be small FWHM emitters S in the context of the present invention. B Where, the PL spectra are measured from spin-coated films of the respective emitter material, typically with an F concentration of 1-5%, preferably 2% by weight, in PMMA.

[0373] The absorption spectra are measured at room temperature (i.e. (approximately) 20° C.) from spin-coated films of the respective materials, typically poly(methyl methacrylate) (PMMA). For the organic molecules according to the invention, typically the TADF material E B In the case of phosphorescent material P B In the case of , the concentration of each substance in the spin-coated PMMA film is 10 wt %, unless otherwise stated. B Not a host material H B whereas the absorption spectrum is typically B In the case of non-molecular fluorescent emitters F of the present invention, in particular, they are considered to be small FWHM emitters S in the context of the present invention. B where F is the absorption spectrum measured from a spin-coated film of each emitter material, typically with a concentration of 1-5%, preferably 2% by weight, of F in PMMA. Alternatively, absorption spectra can also be recorded from a solution of each molecule, for example in dichloromethane or toluene, where the concentration of the solution is generally chosen such that the maximum absorbance is preferably in the 0.1 to 0.5 range.

[0374] Unless otherwise stated, the energy of the first excited triplet state T1 is generally determined from the phosphorescence spectrum onset at 77 K (normal state spectrum) from a spin-coated film of the respective material in poly(methyl methacrylate) (PMMA). B For the organic molecules according to the present invention, the phosphorescence spectra are generally recorded at room temperature (i.e., about 20° C.). B In the case of phosphorescent material P B In the case of , the concentration of each substance in the spin-coated PMMA film is 10 wt %, unless otherwise stated. B Not a host material H B whereas the absorption spectrum is typically B In the case of the non-molecular fluorescent emitters F of the present invention, in particular, they are small FWHM emitters S in the context of the present invention. B where the absorption spectrum is measured from a spin-coated film of each emitter material, typically with an F concentration of 1-5%, preferably 2% by weight in PMMA. ΔE ST TADF material with small value E B In the case of , both intersystem crossing and reverse intersystem crossing can occur even at low temperatures. As a result, the emission spectrum at 77 K contains emission from both the S1 and T1 states. However, the contribution / value of the triplet energy is generally judged to be dominant.

[0375] Unless otherwise stated, the energies of the first excited singlet state S1 are determined from the onset of the fluorescence spectrum (normal state spectrum) at room temperature (i.e. (approximately) 20° C.), typically from spin-coated films of the respective materials in poly(methyl methacrylate) (PMMA). BIn the case of , the concentration of each substance in the spin-coated PMMA film is 10 wt %, unless otherwise stated. B Not a host material H B whereas the absorption spectrum is typically B In the case of the non-molecular fluorescent emitters F of the present invention, in particular, they are small FWHM emitters S in the context of the present invention. B In the case of , the absorption spectra are typically measured from spin-coated films of the respective emitter materials with F concentrations of 1-5%, preferably 2% by weight, in PMMA. However, phosphorescent materials P that exhibit efficient intersystem crossing B In the case of room temperature emission (typically P in PMMA with 10 wt. % of emitter), B The emission spectrum at room temperature (i.e., (approximately) 20° C.) is used to determine the energy of the first excited triplet state T1, but not the energy of the first excited singlet state S1.

[0376] Unless otherwise stated, ΔE corresponds to the energy difference between the first (i.e., lowest) excited singlet state S1 and the first (i.e., lowest) excited triplet state T1. ST The values ​​are determined based on the first excited singlet state energy and the first excited triplet state energy, which are as described above.

[0377] <Example> <General synthesis method I> Illustratively, general synthetic scheme I provides a synthetic scheme for an organic molecule M1 according to the invention.

[0378] JPEG2025503881000073.jpg141170

[0379] General Procedure for Synthesis <aav1> Under a nitrogen atmosphere, dry dioxane is added to E1 (1.00 equivalent, e.g., CAS 109005-10-9), aryl iodide E2 (2.20 equivalent, e.g., CAS 591-50-4), tri-tert-butylphosphonium tetrafluoroborate (0.24 equivalent; CAS 131274-22-1), palladium(II) acetate (0.08 equivalent, CAS 3375-31-3) and sodium tert-butoxide (3.00 equivalent, CAS 865-48-5) and sparged with nitrogen for 10 minutes. The reaction mixture is stirred at 100° C. for 4 hours. After cooling to room temperature, activated charcoal and Celite® (Kieselguhr) are added to the mixture, which is stirred for 15 minutes and then filtered by vacuum suction. The filtrate is extracted with ethyl acetate and brine. The organic extract is concentrated under reduced pressure. The resulting crude product is purified by column chromatography to give P1 as a solid.

[0380] <aav2> Under nitrogen atmosphere, a mixture of toluene / water is added to E3 (1.00 equivalents, e.g., CAS 123843-67-4), boronate E4 (1.10 equivalents, e.g., CAS 24388-23-6), potassium carbonate (2.00 equivalents, CAS 584-08-7), tris(dibenzylideneacetone)dipalladium(0) (0.03 equivalents, CAS 51364-51-3) and X-PHOS (0.12 equivalents, CAS 564483-18-7) and sparged with nitrogen for 10 minutes. The reaction mixture is stirred at 100° C. for 20 hours. After cooling to room temperature, activated charcoal and Celite® (Kieselguhr) are added to the mixture, which is stirred for 15 minutes and then filtered by vacuum suction. The filtrate is extracted with ethyl acetate and brine. The organic extract is concentrated under reduced pressure. The resulting crude product is purified by column chromatography to give P2 as a solid.

[0381] <aav3> P1 (2.2 equiv., product of step 1), P2 (1.00 equiv.) and tripotassium phosphate (5.00 equiv.) are dissolved in dry DMSO under nitrogen atmosphere and stirred at 135 °C for 24-72 h (reaction monitored via LC / MS and TLC). The reaction mixture is then poured into a stirred mixture of water and ice. The resulting precipitate is filtered and washed with water and ethanol. The crude product is purified by column chromatography or recrystallization to give M1 as a solid.

[0382] <General synthesis method II> Illustratively, general synthetic scheme I provides a synthetic scheme for an organic molecule M2 according to the invention.

[0383] JPEG2025503881000074.jpg168170

[0384] General Procedure for Synthesis <aav1> Under a nitrogen atmosphere, dry dioxane is added to E1 (1.00 equivalent, e.g., CAS 109005-10-9), bis(pinacolato)diboron E2 (2.20 equivalent, e.g., CAS 591-50-4), tri-tert-butylphosphonium tetrafluoroborate (0.24 equivalent; CAS 131274-22-1), palladium(II) acetate (0.08 equivalent, CAS 3375-31-3) and sodium tert-butoxide (3.00 equivalent, CAS 865-48-5) and sparged with nitrogen for 10 minutes. The reaction mixture is stirred at 100° C. for 4 hours. After cooling to room temperature, activated charcoal and Celite® (Kieselguhr) are added to the mixture, which is stirred for 15 minutes and then filtered by vacuum suction. The filtrate is extracted with ethyl acetate and brine. The organic extract is concentrated under reduced pressure and the resulting crude product is purified by column chromatography to give P1 as a solid.

[0385] <aav4> Dry THF is added to E5 (1.00 equiv., e.g., CAS 108-77-0) and copper iodide (0.05 equiv., CAS 7681-65-4) under a nitrogen atmosphere, followed by sparging with nitrogen for 10 minutes. The solution is cooled to -20°C, followed by addition of magnesium chloride E6 (2.20 equiv., e.g., CAS 677-22-5). The reaction mixture is stirred at -20°C for 1 hour. Ethanol is added, the mixture is allowed to reach room temperature, then vacuum pumped through a silica pad, washed with cyclohexane and dichloromethane, and filtered. The filtrate is concentrated under reduced pressure. The resulting crude product is purified by recrystallization from heptane and ethanol to give E7 as a solid.

[0386] <aav5> Add a mixture of THF / water to E8 (1.00 equiv., e.g., CAS 123843-67-4), aryl chloride E7 (1.10 equiv., product of step 4), potassium carbonate (2.00 equiv., CAS 584-08-7), tetrakis(triphenylphosphine)palladium(0) (0.05 equiv., CAS 14221-01-3) under nitrogen atmosphere and sparge with nitrogen for 10 minutes. Stir the reaction mixture at reflux for 20 hours. After cooling to room temperature, add activated charcoal and Celite® (Kieselguhr) to the mixture and stir for 15 minutes before filtering by vacuum suction. Extract the filtrate with ethyl acetate and brine. Concentrate the organic extract under reduced pressure. Purify the resulting crude product by recrystallization or column chromatography to give P3 as a solid.

[0387] <aav6> P1 (1.15 equiv., product of step 1), P3 (1.00 equiv.) and tripotassium phosphate (2.00 equiv.) are dissolved in dry DMSO under nitrogen atmosphere and stirred at 120° C. for 14 h (reaction monitored via LC / MS and TLC). The reaction mixture is then poured into a stirred mixture of water and ice. The resulting precipitate is filtered and washed with water, ethanol and heptane. The crude product is purified by column chromatography or recrystallization to give M2 as a solid.

[0388] <Cycling voltage-current method> Cyclic voltage and current measurements were performed on each compound (e.g., organic molecules according to the present invention, general TADF material E) in dichloromethane or a suitable solvent and a suitable supporting electrolyte (e.g., 0.1 mol / L tetrabutylammonium hexafluorophosphate). B , a common host material H B , common phosphorescent material P B , and a common fluorescent emitter F) with a concentration of 10 -3 The measurement is performed in a solution of 1000 mol / L. The measurement is performed in a nitrogen atmosphere at room temperature (i.e., about 20° C.) using a three-electrode assembly (working electrode and counter electrode: Pt wire, reference electrode: Pt wire). 2 / FeCp 2 + Use to correct.

[0389] The HOMO and LUMO data were calibrated using ferrocene as an internal standard, with the literature values ​​of ferrocene used for that purpose.

[0390] <Density functional theory calculation> The molecular structures were optimized using the BP86 function and the Resolution of Identity (RI) approach. The excitation energies were calculated with the Time-Dependent DFT (TD-DFT) method using the (BP86) optimized structures. The orbital energies and excited state energies were calculated with the B3LYP function. For numerical integration, the Def2-SVP basis set and m4-grid were used. The Turbomole program package was used for all calculations.

[0391] <Optical physical measurement> <Sample pretreatment: spin coating> Unless otherwise stated, the photophysical measurements of the components were performed on the respective components in poly(methyl methacrylate) (PMMA) (e.g., organic molecules according to the present invention, the general TADF material E B , a common host material H B , common phosphorescent material P B , and common fluorescent emitters F) from spin-coated films. Unless otherwise stated, the component concentrations of such spin-coated PMMA films are as follows:

[0392] All organic molecules according to the invention: 10% by weight in PMMA A TADF material E as defined herein B : 10% by weight in PMMA A phosphorescent material P as defined herein B : 10% by weight in PMMA Fluorescence emitters F as defined herein, which do not form part of the organic molecules according to the invention, in particular they are small FWHM emitters S in the context of the present invention B In this case: 1 to 5% by weight in PMMA, preferably 2% by weight.

[0393] However, the TADF material E as defined herein is not an organic molecule according to the present invention. B or phosphorescent material P B or a host material H that is not a fluorescent emitter F B In the case of H B A spin-coated neat film of is used in place of the PMMA film.

[0394] Equipment: Spin150, SPS euro Sample concentrations are 1.0 mg / ml and are typically dissolved in a suitable solvent: toluene / DCM.

[0395] Program: 2000 U / min for 7-30 s. After coating, the film was dried at 70°C for 1 min.

[0396] <Absorption measurement> A Thermo Scientific Evolution 201 UV-Visible spectrophotometer is used to determine the maximum absorption wavelength of the sample in the wavelength range above 270 nm, which is used as the excitation wavelength for the measurement of the photoluminescence spectrum and quantum yield.

[0397] <Photoluminescence spectroscopy> For the photoluminescence spectroscopy measurements a Horiba fluorescence spectrometer "Fluoromax 4P" is used.

[0398] Normal-state fluorescence and phosphorescence spectra from phosphorescent emitters are recorded at room temperature. The basic mode of operation is as follows: a continuous light source (a xenon arc lamp) is shone onto an excitation monochromator which selects the appropriate wavelength band. This monochromatic excitation light is directed onto the sample which emits emission light. If the sample is a spin-coated or evaporated film, it is placed in a cuvette (cell) and a nitrogen atmosphere is maintained during the measurement. The emission light is directed to a second emission monochromator which selects a wavelength band that is changed during the measurement and shines onto a photon-counting detector (R928P photomultiplier tube). The signal from the detector is reported to a system controller and host computer which can process and display the data.

[0399] Phosphorescence spectra from the TADF emitter are recorded at 77 K. The basic operating scheme is as follows: For excitation, a pulsed light source (pulsed xenon lamp) is used, operating at 25 Hz. A control module containing a gate and delay generator is used to control the timing between excitation and sensing. A typical data collection sequence starts with a flash of the pulsed lamp, which is sensed by the control module. Light enters and is dispersed into the excitation monochromator. Monochromatic light from the monochromator excites the sample. The sample is placed in a glass Dewar vessel filled with liquid nitrogen during the measurement. Light emission from the sample is transmitted through the emission monochromator to a photon-counting photomultiplier-tube detector. The control module intercepts the signal from the detector and collects only the gated portion of the signal after the flash (initial delay) for the length of a predefined sampling time (sample window). All signals arriving before and after the gating are ignored. The initial delay can be varied from 0 to 10000 ms and is set to eliminate the effects of initial fluorescent emission and lamp decay, and is preferably 50 ms. The sample window can be varied from 0.01 to 10000 ms and is set to collect phosphorescent emission, and is preferably 40 ms.

[0400] <Time-resolved (transient) photoluminescence (PL) spectroscopy in the μs and ns ranges (FS5)> Time-resolved PL measurements are performed on an Edinburgh Instruments FS5 fluorescence spectrometer. Better light collection compared to measurements on the HORIBA device allows an optimized signal to noise ratio, which is particularly advantageous for the FS5 system in transient PL measurements of delayed fluorescence properties. As a continuous light source the spectrometer contains a 150W xenon arc lamp, the specific wavelength being selected by a Czerny-Turner monochromator. However, standard measurements are instead performed using an external VPLED tunable pulsed LED with an emission wavelength of 310 nm. The sample emission is directed to a sensitive R928P photomultiplier tube (PMT) that can detect single photons with a peak quantum efficiency of up to 25% in the spectral range from 200 nm to 870 nm. The detector is a temperature-stabilized PMT that provides dark counts of less than 300 cps (counts per second).

[0401] Data collection is performed using the well-established Time Correlated Single Photon Counting (TCSPC) technique. The FS5 is equipped with an emission monochromator, a temperature stabilized photomultiplier tube as the detector unit, and a pulsed LED (310 nm central wavelength, 910 ps pulse width) as the excitation source. If the sample is a spin-coated or evaporated film, it is placed in a cuvette and a nitrogen atmosphere is maintained during the measurement.

[0402] Mean decay lifetime of measured transient photoluminescence signals To determine JPEG2025503881000075.jpg7170, the data is fitted to the following sum of n exponential functions:

[0403] JPEG2025503881000076.jpg13170

[0404] Here, n is 1 to 3. JPEG2025503881000077.jpg6170 with the corresponding amplitude JPEG2025503881000078.jpg7170 Weighting by delayed fluorescence lifetime JPEG2025503881000079.jpg5170 is determined to be:

[0405] JPEG2025503881000080.jpg13170

[0406] <Time-Correlated Single Photon Counting (TCSPC)> The excited state distribution dynamics are determined using an Edinburgh Instruments FS5 spectrofluorometer equipped with an emission monochromator, a temperature stabilized photomultiplier tube as the detector unit, and a pulsed LED (310 nm central wavelength, 910 ps pulse width) as the excitation source. Samples are placed in cuvettes and flushed with nitrogen during the measurements.

[0407] <Overall damping dynamics> The entire excited state population decay dynamics over multiple orders of magnitude in time and signal intensity is achieved by performing TCSPC measurements in four time domains (200 ns, 1 μs, 20 μs and longer measurement periods of >80 μs). The measured time curves are then processed in the following manner:

[0408] 1. The average signal level before excitation and subtracting is determined and background correction is applied. 2. The initial rise of the main signal is taken as the reference and the time axis is aligned. 3. Using the superimposed measured time domains, the curves are scaled relative to each other. 4. The processed curves are merged into one curve.

[0409] <Data Analysis> Data analysis is performed using mono- and bi-exponential fitting of the immediate fluorescence (PF) (typically on the order of nanoseconds) and delayed fluorescence (DF) (typically on the order of microseconds) decays. The ratio of delayed to immediate fluorescence (n value) is calculated by integrating the respective photoluminescence decays over time:

[0410] JPEG2025503881000081.jpg14170

[0411] The mean excited state lifetime is calculated by taking the average of the decay times of the prompt and delayed fluorescence weighted by the respective contributions of PF and DF.

[0412] <Photoluminescence quantum yield measurement> For photoluminescence quantum yield (PLQY) measurements, an Absolute PL quantum yield measurement C9920-03G system (Hamamatsu Photonics) was used. Quantum yields and CIE coordinates were determined using the software U6039-05 version 3.6.0.

[0413] Emission maxima are given in nm, quantum yields Φ are given in %, and CIE coordinates are given as x,y values.

[0414] The PLQY is determined using the following protocol: 1) Quality assurance: Anthracene in ethanol (known concentration) is used as a standard.

[0415] 2) Excitation wavelength: The absorption maximum of the organic molecule is determined and that wavelength is used to excite the molecule.

[0416] 3) Measurement The quantum yield is measured at room temperature (i.e., about 20° C.) from the spin-coated films as described above in a nitrogen atmosphere. The PLQY is calculated using the following equation:

[0417] JPEG2025503881000082.jpg21170

[0418] where n 光子 denotes the number of photons, and I denotes the intensity. The designation "reference" denotes a reference measurement without a luminescent sample, and the designation "sample" denotes a measurement with a luminescent sample. The wavelength λ 1 and λ 2 denotes the excitation light region, and the wavelength λ 3 and λ 4 displays the sample emission area.

[0419] <Fabrication and characterization of optoelectronic devices> The optoelectronic device, particularly the OLED device, comprising the organic molecules according to the present invention can be manufactured by vacuum deposition method. When a layer comprises one or more compounds, the weight percentage of one or more compounds is indicated in %. The total weight percentage value is 100%, so when no value is specified, the fraction of the compound is the same as the difference between the specified value and 100%.

[0420] Non-fully optimized OLEDs are characterized by measuring the electroluminescence spectrum using standard methods and the intensity- and current-dependent external quantum efficiency (%) calculated using the light and current detected by a photodiode. The lifetime of the OLED device is extracted from the change in luminance while operating at a constant current density. The LT50 value corresponds to the time when the measured luminance has decreased to 50% of the initial luminance, similarly LT80 corresponds to the point when the measured luminance has decreased to 80% of the initial luminance, and LT97 corresponds to the point when the measured luminance has decreased to 97% of the initial luminance.

[0421] Accelerated lifetime measurements are performed (e.g. by applying increased current densities), e.g. 500cd / m 2 In the present invention, the LT80 value is determined using the following formula:

[0422] JPEG2025503881000083.jpg22170

[0423] Here, L 0 denotes the initial luminance at an applied current density.

[0424] Values ​​refer to the average of multiple pixels (typically 2-8) and the standard deviation across the pixels is provided. The figures show the data series for one OLED pixel.

[0425] <hplc-ms> The purity of organic compounds may be assessed using high pressure liquid chromatography (HPLC) coupled with mass spectrometry (MS). Such HPLC-MS analysis is performed using an Agilent HPLC1260 infinity HPLC-MS system equipped with a single quadrupole MS detector. For example, a typical HPLC method is as follows: a reversed phase column 3.0 mm×100 mm, particle size 2.7 μm Agilent (Poroshell 120EC-C18, 3.0×100 mm, 2.7 μm HPLC column) is used for the HPLC. The HPLC-MS measurements are performed at 45° C. with a typical gradient as follows:

[0426] [Table 1]

[0427] The following solvent mixtures were also used (all solvents contained 0.1% (V / V) formic acid):

[0428] [Table 2]

[0429] From an analyte solution of 0.5 mg / mL concentration, an injection volume of 2 μL is used for the measurement.

[0430] Ionization of the probe is performed in an APCI (atmospheric pressure chemical ionization) source using positive (APCI+) or negative (APCI-) ionization mode, or using an APPI (atmospheric pressure photoionization) source.

[0431] <Example 1> JPEG2025503881000086.jpg91170

[0432] Example 1 was synthesized by: AAV1 (36% yield), where 10,15-dihydro-5H-diindolo[3,2-a:3',2'-c]carbazole (CAS 109005-10-9) was used as reactant E1 and iodobenzene (CAS 591-50-4) was used as reactant E2.

[0433] AAV2 (46% yield), where 4-bromo-2,6-difluorobenzonitrile (CAS: 123843-67-4) was used as reactant E3 and phenylboronic acid pinacol ester (CAS: 24388-23-6) was used as reactant E4.

[0434] AAV3 (yield 19%).

[0435] MS (HPLC-MS), m / z (residence time): 1170 (6.3 minutes).

[0436] At room temperature (i.e., about 20° C.), the emission spectrum of Example 1 (10 wt % in PMMA) had an emission maximum (λ max The photoluminescence quantum yield (PLQY) is 57% and the delayed fluorescence lifetime determined from a 20 μs measurement window is 1.8 μs. The resulting CIE x The coordinates were determined to be 0.31, CIE y The coordinate is determined to be 0.52.

[0437] <Example 2> JPEG2025503881000087.jpg59170

[0438] Example 2 was synthesized by: AAV2 (46% yield), where 4-bromo-2,6-difluorobenzonitrile (CAS: 123843-67-4) was used as reactant E3 and phenylboronic acid pinacol ester (CAS: 24388-23-6) was used as reactant E4.

[0439] AAV3 (yield 33%), where 5,11-dihydro-5-phenylindolo[3,2-b]carbazole (CAS 1316311-27-9) was used as reactant P2.

[0440] MS (HPLC-MS), m / z (residence time): 841 (4.9 minutes).

[0441] At room temperature (i.e., about 20° C.), the emission spectrum of Example 2 (10 wt % in PMMA) had an emission maximum (λ max The photoluminescence quantum yield (PLQY) is 64% and the delayed fluorescence lifetime determined from a 20 μs measurement window is 6.6 μs. x The coordinates are determined in 0.22 and CIE y The coordinates are determined by 0.38.

[0442] <Example 3> JPEG2025503881000088.jpg78170

[0443] AAV1 (36% yield), where 10,15-dihydro-5H-diindolo[3,2-a:3',2'-c]carbazole (CAS 109005-10-9) was used as reactant E1 and iodobenzene (CAS 591-50-4) was used as reactant E2.

[0444] AAV5 (81% yield), where 3-cyano-4-fluorophenylboronic acid (CAS: 214210-21-6) was used as reactant E8 and 2-chloro-4,6-diphenyl-1,3,5-triazine (CAS: 3842-55-5) was used as reactant E7.

[0445] AAV6 (yield 53%).

[0446] MS (HPLC-MS), m / z (residence time): 830 (5.8 minutes).

[0447] At room temperature (i.e., about 20° C.), the emission spectrum of Example 3 (10 wt % in PMMA) had an emission maximum (λ max The photoluminescence quantum yield (PLQY) is 31% and the delayed fluorescence lifetime determined from a 20 μs measurement window is 1.1 μs. The resulting CIE x The coordinate was determined to be 0.41, CIE y The coordinate is determined to be 0.45.

[0448] <Example 4> JPEG2025503881000089.jpg78170

[0449] AAV1 (36% yield), where 10,15-dihydro-5H-diindolo[3,2-a:3',2'-c]carbazole (CAS 109005-10-9) was used as reactant E1 and iodobenzene (CAS 591-50-4) was used as reactant E2.

[0450] AAV5 (90% yield), where 3-cyano-4-fluorophenylboronic acid (CAS: 214210-21-6) was used as reactant E8 and 4-chloro-2,6-diphenylpyrimidine (CAS: 29509-91-9) was used as reactant E7.

[0451] AAV3 (yield 33%).

[0452] MS (HPLC-MS), m / z (residence time): 830 (5.7 minutes).

[0453] At room temperature (i.e., about 20° C.), the emission spectrum of Example 4 (10 wt % in PMMA) had an emission maximum at 522 nm (λ max The photoluminescence quantum yield (PLQY) is 59% and the delayed fluorescence lifetime determined from a 20 μs measurement window is 2.0 μs. The resulting CIE x The coordinate was determined to be 0.32, CIE y The coordinate is determined to be 0.53.

[0454] <Example 5> JPEG2025503881000090.jpg74170

[0455] AAV1 (yield 36%), where 10,15-dihydro-5H-diindolo[3,2-a:3’,2’-c]carbazole (CAS 109005-10-9) was used as reactant E1 and iodobenzene (CAS 591-50-4) was used as reactant E2.

[0456] AAV4 (yield 62%), where cyanuric chloride (CAS 108-77-0) was used as reactant E5 and tert-butylmagnesium chloride (CAS 677-22-5) was used as reactant E6.

[0457] AAV5 (yield 95%), where 3-cyano-4-fluorophenylboronic acid (CAS: 214210-21-6) was used as reactant E8 and the product of AAV4 (62%) was used as reactant E7.

[0458] AAV6 (yield 82%).

[0459] MS (HPLC-MS), m / z (retention time): 791 (6.5 minutes).

[0460] At room temperature (i.e., about 20 °C), the emission spectrum of Example 5 (10 wt% in PMMA) has a maximum emission at 524 nm (λ max ) and has. The photoluminescence quantum yield (PLQY) is 48%, and the delayed fluorescence lifetime determined from a 20 μs measurement window is 1.4 μs. The resulting CIE x coordinates are determined to be 0.34, and the CIE y coordinates are determined to be 0.53.

[0461] <OLED device example> <Stack material> JPEG2025503881000091.jpg19170Liq

[0462] JPEG2025503881000092.jpg57170NPB

[0463] JPEG2025503881000093.jpg56170NDP-9

[0464] JPEG2025503881000094.jpg55170ETM1 (electron transport material)

[0465] JPEG2025503881000095.jpg38170ETM2 (electron transport material)

[0466] JPEG2025503881000096.jpg68170EBM1 (electron blocking substance)

[0467] JPEG2025503881000097.jpg54170Host1(host substance)

[0468] JPEG2025503881000098.jpg45170Phos1 (phosphorescent substance)

[0469] JPEG2025503881000099.jpg66170Fluo1 (fluorescent substance)

[0470] Example 4 was tested on OLED D1 and OLED D2, which were fabricated with the following layer structure:

[0471] [Table 3]

[0472] The OLED D1 is 1000cd / m 2 The device exhibited an external quantum efficiency (EQE) of 21.9% at 4.0 V. The emission maximum was 532 nm with a FWHM of 92 nm at 4.0 V. The corresponding CIEx value was 0.351 and CIEy value was 0.581. 2 The relative lifetime LT97 value at is 1.0 hour.

[0473] OLED D2 is 1000cd / m 2 The device exhibited an external quantum efficiency (EQE) of 20.5% at 4.9 V. The emission maximum was 526 nm with a FWHM of 80 nm. The corresponding CIEx value was 0.349 and CIEy value was 0.603. 2 The relative life span LT97 value in is 31.2 hours.

[0474] Example 4 was tested on an OLED D3 made with the following layer structure:

[0475] [Table 4]

[0476] OLED D3 is 1000cd / m 2 The device exhibited an external quantum efficiency (EQE) of 26.1% at 4.9 V. The emission maximum was 532 nm with a FWHM of 42 nm at 4.9 V. The corresponding CIEx value was 0.323 and CIEy value was 0.641. 2 The relative life span LT97 value in is 59.8 hours.

[0477] <Additional Examples of Organic Molecules of the Present Invention> JPEG2025503881000102.jpg168170

[0478] JPEG2025503881000103.jpg168170

[0479] JPEG2025503881000104.jpg169170

[0480] JPEG2025503881000105.jpg169170

[0481] JPEG2025503881000106.jpg170170

[0482] JPEG2025503881000107.jpg169170

[0483] JPEG2025503881000108.jpg168170

[0484] JPEG2025503881000109.jpg169170

[0485] JPEG2025503881000110.jpg169170

[0486] JPEG2025503881000111.jpg169170

[0487] JPEG2025503881000112.jpg168170

[0488] JPEG2025503881000113.jpg169170

[0489] JPEG2025503881000114.jpg169170

[0490] JPEG2025503881000115.jpg168170

[0491] JPEG2025503881000116.jpg169170

[0492] JPEG2025503881000117.jpg170170

[0493] JPEG2025503881000118.jpg170170

[0494] JPEG2025503881000119.jpg169170

[0495] JPEG2025503881000120.jpg172170

[0496] JPEG2025503881000121.jpg170170

[0497] JPEG2025503881000122.jpg169170

[0498] JPEG2025503881000123.jpg169170

Claims

1. a first chemical moiety comprising the structure of Formula I, and [Chemical formula I] An organic molecule comprising one or two second chemical moieties comprising the structure of Formula II: [Chemical formula II] Where: n, in each occurrence, is independently selected from the group of integers consisting of 1 and 2; the first chemical moiety is linked to each of the second chemical moieties through a single bond; T, V, W, X and Y are R １ and a single bond attachment site linking the first chemical moiety to the second chemical moiety; # indicates a binding site between the first chemical moiety and the second chemical moiety; Z in each occurrence independently represents a direct bond, CR ３ R ４ , C=CR ３ R ４ , C=O, C=NR ３ , N.R. ３ , O, SiR ３ R ４ , S, S(O) and S(O) ２ is selected from the group consisting of Z § are, in each case independently of one another, NR ５ , O and S; R １ are each independently selected from the group consisting of (a1) to (a6): (a1) Hydrogen, deuterium, CN, CF ３ , phenyl, (a2) C １ -C ５ Alkyl, wherein optionally one or more hydrogen atoms are replaced with deuterium; (a3) C ２ -C ８ Alkenyl, wherein optionally one or more hydrogen atoms are replaced with deuterium; (a4) C ２ -C ８ Alkynyl, wherein optionally one or more hydrogen atoms are replaced with deuterium; (a5) optionally one or more substituents R ５ C substituted with ６ -C １８ Aryl, and (a6) optionally one or more substituents R ５ C substituted with ３ -C １７ Heteroaryl, R ａ , R ３ and R ４ are each independently selected from the group consisting of (b1) to (b19): (b1) hydrogen, (b2) deuterium, (b3) N(R ５ ) ２ 、 (b4) OR ５ 、 (b5) Si(R ５ ) ３ 、 (b6) B(OR ５ ) ２ 、 (b7) OSO ２ R ５ 、 (b8) CF ３ 、 (b9) C.N., (b10) F, (b11) Br, (b12) I, (b13) C １ -C ４０ Alkyl, This may optionally include one or more substituents R ５ is replaced by Here, one or more non-adjacent CH ２ The group is optionally R ５ C=CR ５ , C≡C, Si(R ５ ) ２ , Ge(R ５ ) ２ , Sn(R ５ ) ２ , C=O, C=S, C=Se, C=NR ５ , P(=O)(R ５ ), SO, SO ２ , N.R. ５ , O, S or CONR ５ is replaced by (b14) C １ -C ４０ Alkoxy, This may optionally include one or more substituents R ５ is replaced by Here, one or more non-adjacent CH ２ The group is optionally R ５ C=CR ５ , C≡C, Si(R ５ ) ２ , Ge(R ５ ) ２ , Sn(R ５ ) ２ , C=O, C=S, C=Se, C=NR ５ , P(=O)(R ５ ), SO, SO ２ , N.R. ５ , O, S or CONR ５ is replaced by (b15) C １ -C ４０ Thioalkoxy, This may optionally include one or more substituents R ５ is replaced by Here, one or more non-adjacent CH ２ The group is optionally R ５ C=CR ５ , C≡C, Si(R ５ ) ２ , Ge(R ５ ) ２ , Sn(R ５ ) ２ , C=O, C=S, C=Se, C=NR ５ , P(=O)(R ５ ), SO, SO ２ , N.R. ５ , O, S or CONR ５ is replaced by (b16) C ２ -C ４０ Alkenyl, This may optionally include one or more substituents R ５ is replaced by Here, one or more non-adjacent CH ２ The group is optionally R ５ C=CR ５ , C≡C, Si(R ５ ) ２ , Ge(R ５ ) ２ , Sn(R ５ ) ２ , C=O, C=S, C=Se, C=NR ５ , P(=O)(R ５ ), SO, SO ２ , N.R. ５ , O, S or CONR ５ is replaced by (b17) C ２ -C ４０ Alkynyl, This may optionally include one or more substituents R ５ is replaced by Here, one or more non-adjacent CH ２ The group is optionally R ５ C=CR ５ , C≡C, Si(R ５ ) ２ , Ge(R ５ ) ２ , Sn(R ５ ) ２ , C=O, C=S, C=Se, C=NR ５ , P(=O)(R ５ ), SO, SO ２ , N.R. ５ , O, S or CONR ５ is replaced by (b18) optionally one or more substituents R ５ C substituted with ６ -C ６０ Aryl, and (b19) optionally one or more substituents R ５ C substituted with ３ -C ５７ Heteroaryl, R ５ are each independently selected from the group consisting of (c1) to (c8): (c1) Hydrogen, deuterium, N(R ６ ) ２ , OR ６ , Si(R ６ ) ３ , B(OR ６ ) ２ , OSO ２ R ６ , C.F. ３ ,CN,F,Br,I, (c2) C １ -C ４０ Alkyl, This may optionally include one or more substituents R ６ is replaced by Here, one or more non-adjacent CH ２ The group is optionally R ６ C=CR ６ , C≡C, Si(R ６ ) ２ , Ge(R ６ ) ２ , Sn(R ６ ) ２ , C=O, C=S, C=Se, C=NR ６ , P(=O)(R ６ ), SO, SO ２ , N.R. ６ , O, S or CONR ６ is replaced by (c3) C １ -C ４０ Alkoxy, This may optionally include one or more substituents R ６ is replaced by Here, one or more non-adjacent CH ２ The group is optionally R ６ C=CR ６ , C≡C, Si(R ６ ) ２ , Ge(R ６ ) ２ , Sn(R ６ ) ２ , C=O, C=S, C=Se, C=NR ６ , P(=O)(R ６ ), SO, SO ２ , N.R. ６ , O, S or CONR ６ is replaced by (c4) C １ -C ４０ Thioalkoxy, This may optionally include one or more substituents R ６ is replaced by Here, one or more non-adjacent CH ２ The group is optionally R ６ C=CR ６ , C≡C, Si(R ６ ) ２ , Ge(R ６ ) ２ , Sn(R ６ ) ２ , C=O, C=S, C=Se, C=NR ６ , P(=O)(R ６ ), SO, SO ２ , N.R. ６ , O, S or CONR ６ is replaced by (c5) C ２ -C ４０ Alkenyl, This may optionally include one or more substituents R ６ is replaced by Here, one or more non-adjacent CH ２ The group is optionally R ６ C=CR ６ , C≡C, Si(R ６ ) ２ , Ge(R ６ ) ２ , Sn(R ６ ) ２ , C=O, C=S, C=Se, C=NR ６ , P(=O)(R ６ ), SO, SO ２ , N.R. ６ , O, S or CONR ６ is replaced by (c6) C ２ -C ４０ Alkynyl, This may optionally include one or more substituents R ６ is replaced by Here, one or more non-adjacent CH ２ The group is optionally R ６ C=CR ６ , C≡C, Si(R ６ ) ２ , Ge(R ６ ) ２ , Sn(R ６ ) ２ , C=O, C=S, C=Se, C=NR ６ , P(=O)(R ６ ), SO, SO ２ , N.R. ６ , O, S or CONR ６ is replaced by (c7) optionally one or more substituents R ６ C substituted with ６ -C ６０ Aryl, and (c8) optionally one or more substituents R ６ C substituted with ３ -C ５７ Heteroaryl, R ６ are each independently selected from the group consisting of (d1) to (d11) below: (d1) Hydrogen, deuterium, OPh, CF ３ ,C.N.,F. (d2) C １ -C ５ Alkyl, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF ３ or is substituted by F, (d3) C １ -C ５ Alkoxy, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF ３ or is substituted by F, (d4) C １ -C ５ Thioalkoxy, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF ３ or is substituted by F, (d5) C ２ -C ５ Alkenyl, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF ３ or is substituted by F, (d6) C ２ -C ５ Alkynyl, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF ３ or is substituted by F, (d7) Optionally, one or more C １ -C ５ C substituted with alkyl substituents ６ -C １８ Aryl, (d8) Optionally, one or more C １ -C ５ C substituted with alkyl substituents ３ -C １７ Heteroaryl, (d9) N (C ６ -C １８ Aryl) ２ , (d10) N (C ３ -C １７ Heteroaryl) ２ , and (d11) N (C ３ -C １７ Heteroaryl) (C ６ -C １８ Aryl), Where: substituent R ａ , R ３ , R ４ Or R ５ are, independently of one another, one or more substituents R ａ , R ３ , R ４ Or R ５ together optionally forming a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system, Where: Exactly one substituent selected from the group T, V, W, X, and Y is a single bond attachment site linking the first chemical moiety to the second chemical moiety; or Exactly two substituents selected from the group T, V, W, X, and Y are each a single bond attachment site linking the first chemical moiety to one of the second chemical moieties.

2. 2. The organic molecule of claim 1 , wherein the second moiety is independently selected from the group consisting of Formula IIIa, Formula IIIb, Formula IIIc, Formula IIIe, Formula IIIf, and Formula IIIg: [Chemical formula IIIa] [Chemical formula IIIb] [Chemical formula IIIc] [Chemical formula IIId] [Chemical formula IIIe] [Chemical formula IIIf] [Chemical formula IIIg] 。

3. R ａ and R ５ is, in each case independently of one another, selected from the group consisting of: hydrogen, deuterium, Me, ｉ Pr、 ｔ This, C.N., CF ３ 、 Me, ｉ P.R. ｔ Bu, C.N., C.F. ３ Ph optionally substituted with one or more substituents independently selected from the group consisting of Me, ｉ P.R. ｔ Bu, C.N., C.F. ３ pyridinyl optionally substituted with one or more substituents independently selected from the group consisting of: Me, ｉ P.R. ｔ Bu, C.N., C.F. ３ pyrimidinyl optionally substituted with one or more substituents independently selected from the group consisting of: Me, ｉ P.R. ｔ Bu, C.N., C.F. ３ and Ph; Me, ｉ P.R. ｔ Bu, C.N., C.F. ３ and Ph, Me, ｉ P.R. ｔ Bu, C.N., C.F. ３ N(Ph) optionally substituted with one or more substituents independently selected from the group consisting of ２ .

4. 4. The organic molecule of claim 1 , wherein Z is a direct bond.

5. The organic molecule of claim 1 , wherein the second moiety independently comprises a structure according to Formula IVa: [Chemical formula IVa] Where: p, in each occurrence, is independently an integer selected from the group consisting of 1, 2, 3, 4, and 5; R ６ are, in each occurrence, independently selected from the group consisting of: hydrogen, deuterium, Me, ｉ Pr、 ｔ This, C.N., CF ３ 、 Me, ｉ P.R. ｔ Bu, C.N., C.F. ３ Ph optionally substituted with one or more substituents independently selected from the group consisting of Me, ｉ P.R. ｔ Bu, C.N., C.F. ３ pyridinyl optionally substituted with one or more substituents independently selected from the group consisting of: Me, ｉ P.R. ｔ Bu, C.N., C.F. ３ pyrimidinyl optionally substituted with one or more substituents independently selected from the group consisting of: Me, ｉ P.R. ｔ Bu, C.N., C.F. ３ and Ph; Me, ｉ P.R. ｔ Bu, C.N., C.F. ３ and Ph, Me, ｉ P.R. ｔ Bu, C.N., C.F. ３ N(Ph) optionally substituted with one or more substituents independently selected from the group consisting of ２ .

6. 6. The organic molecule of claim 1 , comprising a structure selected from the group consisting of formula Ia, formula Ib, formula Ic, and formula Id: [Chemical formula Ia] [Chemical formula Ib] [Chemical formula Ic] [Chemical formula Id] where § denotes a single bond attachment site linking the first chemical moiety to one of the second chemical moieties.

7. 6. The organic molecule of claim 1 , comprising a structure selected from the group consisting of Formula IIa, Formula IIb, and Formula IIc: [Chemical formula IIa] [Chemical formula IIb] [Chemical formula IIc] where § denotes a single bond attachment site linking a first chemical moiety to a second chemical moiety.

8. The organic molecule of any one of claims 1 to 5, comprising a structure selected from the group consisting of: [Chemical formula Va] [Chemical formula Vb] [Chemical formula Vc] Where: § denotes a single bond attachment site linking the first chemical moiety to one of the second chemical moieties; R Ａ is selected from the group consisting of: ・CN、CF ３ 、 Optionally, one or more substituents R ５ C substituted with ６ -C １８ Aryl, and Optionally, one or more substituents R ５ C substituted with ３ -C １７ Heteroaryl, R ２ is hydrogen, deuterium, Me, ｉ P.R. ｔ It is selected from the group consisting of Bu and Ph.

9. An optoelectronic device comprising an organic molecule according to any one of claims 1 to 8.

10. The optoelectronic device of claim 9, wherein the optoelectronic device is selected from the group consisting of: Organic Light Emitting Diodes (OLEDs), - light-emitting electrochemical cells, OLED sensors, - organic diodes, ・Organic solar cells, - Organic transistors, - organic field effect transistors, Organic lasers, and ・Down conversion element.

11. 11. The optoelectronic device according to claim 9 or 10, wherein the optoelectronic device is an organic light emitting diode comprising the organic molecules in an emissive layer (EML) and / or in a layer directly adjacent to the emissive layer (EML).

12. A composition comprising: - an organic molecule according to any one of claims 1 to 8, - a host material H different from the organic molecule Ｂ .

13. A fluorescent emitter F and / or a phosphorescent substance P different from the organic molecule Ｂ Further comprising: Here, the ratio (wt%) of the organic molecules is the ratio of the fluorescent emitter F and / or the phosphorescent material P Ｂ The composition of claim 12, wherein the proportion (wt%) is greater than or equal to 100%.

14. 14. A method for the manufacture of an optoelectronic device, in which an organic molecule according to any one of claims 1 to 8 or a composition according to claim 12 or 13 is used, in particular comprising a step of processing said organic molecule using a vacuum deposition method or from a solution.

15. (i) providing an optoelectronic device according to any one of claims 9 to 11; (ii) applying a current to said element.

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