Organic molecules for optoelectronic devices

Abstract

This invention relates to organic molecules for use in optoelectronic devices. The organic molecules have the structure of formula I: wherein R... a Each time it appears, choose from the following group: hydrogen, deuterium, N(R) 5 2. OR 5 SR 5 CF3, CN, halogens, C1-C 40 -alkyl, C1-C 40 -alkoxy, C1-C 40 -Thioalkoxy, C6-C 60 -Aryl and C3-C 57 - Heteroaryl; and R I R II R III R IV R V R VI R VII R VIII R IX R X and R XI Each time it appears, it is independently selected from the following groups: hydrogen, deuterium, N(R) 4 2. OR 4 SR 4 Si(R) 4 3. B(OR) 4 2. OSO2R 4 CF3, CN, halogens, C1-C 40 -alkyl, C1-C 40 -alkoxy, C1-C 40 -Thioalkoxy, C6-C 60 -Aryl and C3-C 57 - Mixed aromatic compounds.

Description

Technical Field

[0001] This invention relates to organic molecules and their use in organic light-emitting diodes (OLEDs) and other optoelectronic devices. Background Technology

[0002] Optoelectronic devices containing one or more organic-based light-emitting layers, such as organic light-emitting diodes (OLEDs), light-emitting electrochemical cells (LECs), and light-emitting transistors, are becoming increasingly important. In particular, OLEDs are promising devices for electronic products such as screens, displays, and lighting devices. Compared to most electroluminescent devices that are essentially inorganic, organic optoelectronic devices based on organic materials are generally quite flexible and can be fabricated into particularly thin layers. Currently available OLED-based screens and displays exhibit good efficiency and long lifespan, or good color purity and long lifespan, but none combine all three properties: good efficiency, long lifespan, and good color purity.

[0003] Therefore, there remains an unmet technological need for optoelectronic devices with high quantum yield, long lifetime and good color purity.

[0004] The color purity or color point of an OLED is typically provided by CIEx and CIEy coordinates, while the color gamut of next-generation displays is provided by so-called BT-2020 and DCPI3 values. Generally, to achieve these color coordinates, a top-emitting device is required to adjust the color coordinates by changing the cavity. To achieve high efficiency while simultaneously targeting this color gamut in a top-emitting device, a narrow emission spectrum is needed within the top-emitting device. Summary of the Invention

[0005] The purpose of this invention is to provide molecules suitable for optoelectronic devices.

[0006] This objective is achieved by providing the present invention, which provides a new class of organic molecules.

[0007] The organic molecules according to the invention exhibit emission maximum values ​​in the deep blue, sky blue, or green spectral range, preferably in the deep blue and sky blue spectral range, and most preferably in the deep blue spectral range. The organic molecules particularly exhibit emission maximum values ​​from 420 nm to 520 nm, preferably from 440 nm to 495 nm, and more preferably from 450 nm to 475 nm. The photoluminescence quantum yield of the organic molecules according to the invention is particularly 50% or greater than 50%. The excited-state lifetime is not greater than 4 μs. Furthermore, the molecules of the invention particularly exhibit narrow emission, characterized by a small full width at half maximum (FWHM). Unless otherwise stated, the emission spectrum of the organic molecules preferably shows a FWHM less than or equal to 0.15 eV (≤0.15 eV), measured at room temperature (i.e., about 25 °C) using 2% by weight of poly(methyl methacrylate) PMMA as the emitter. The photoluminescence quantum yield of the organic molecules according to the invention is particularly 50% or greater than 50%.

[0008] The use of the organic molecules according to the invention in optoelectronic devices (e.g., organic light-emitting diodes (OLEDs)) results in narrow emission and high efficiency. The corresponding OLEDs exhibit higher stability than OLEDs containing known emitter materials and comparable colors, and / or, by using the organic molecules according to the invention in OLED displays, more accurate reproduction of visible colors in nature is achieved, i.e., higher resolution in displayed images. In particular, the molecules can be used in combination with energy pumps to achieve strong fluorescence or strong phosphorescence. In these cases, another substance contained in the optoelectronic device transfers energy to the organic molecules of the invention, which then emit light.

[0009] The organic molecules according to the present invention comprise or consist of the structure of Formula I:

[0010]

[0011] in

[0012] R a Each time it appears, independently select from the following groups:

[0013] Hydrogen, deuterium, N(R) 5 2. OR 5 SR 5 CF3, CN, halogens

[0014] C1-C 40 -alkyl,

[0015] The C1-C 40 -The alkyl group is optionally replaced by one or more substituents R 5 Replacement, and

[0016] One or more non-adjacent CH2- groups are optionally R 5 C = CR 5 C≡C, Si(R) 5 )2、Ge(R 5 )2、Sn(R 5 )2. C=O, C=S, C=Se, C=NR 5 、P(=O)(R 5 SO, SO2, NR 5 O, S or CONR 5 replace;

[0017] C1-C 40 -alkoxy,

[0018] The C1-C 40 -Alkoxy group is optionally replaced by one or more substituents R 5 Replacement, and

[0019] One or more non-adjacent CH2- groups are optionally R 5 C = CR 5 C≡C, Si(R) 5 )2、Ge(R 5 )2、Sn(R 5 )2. C=O, C=S, C=Se, C=NR 5 、P(=O)(R 5 SO, SO2, NR 5 O, S or CONR 5 replace;

[0020] C1-C 40 -Thioalkoxy,

[0021] The C1-C 40 -Thioalkoxy group is optionally replaced by one or more substituents R 5 Replacement, and

[0022] One or more non-adjacent CH2- groups are optionally R 5 C = CR 5 C≡C, Si(R) 5 )2、Ge(R 5 )2、Sn(R 5 )2. C=O, C=S, C=Se, C=NR 5 、P(=O)(R 5 SO, SO2, NR 5 O, S or CONR 5 replace;

[0023] C6-C 60 -Aryl

[0024] The C6-C 60 -The aryl group is optionally replaced by one or more substituents R 5 Replace; and

[0025] C3-C 57 - heteroaryl

[0026] The C3-C 57 -The heteroaryl group is optionally replaced by one or more substituents R 5 replace;

[0027] R 5 Each time it appears, independently select from the following groups:

[0028] Hydrogen, deuterium, halogens,

[0029] C1-C 12 -alkyl,

[0030] In which one or more hydrogen atoms are independently controlled by R 6 replace;

[0031] C6-C 18 -Aryl

[0032] In which one or more hydrogen atoms are independently controlled by R 6 Replace; and

[0033] C3-C 15 - heteroaryl

[0034] In which one or more hydrogen atoms are independently controlled by R 6 replace;

[0035] R 6 Each time it appears, independently select from the following groups:

[0036] Hydrogen, deuterium, halogens, C1-C 12 -alkyl,

[0037] C6-C 18 -Aryl

[0038] Optionally, one or more hydrogen atoms are independently substituted with C1-C5-alkyl substituents; and

[0039] C3-C 15 - heteroaryl

[0040] Optionally, one or more hydrogen atoms are independently substituted by C1-C5-alkyl substituents;

[0041] R I R II R III R IV R V R VI R VII R VIII R IX R X and R XI Each time it appears, independently select from the following groups:

[0042] Hydrogen, deuterium, N(R) 4 2. OR 4 SR 4 Si(R) 4 3. B(OR) 4 2. OSO2R 4 CF3, CN, halogens

[0043] C1-C 40 -alkyl,

[0044] The C1-C 40 -The alkyl group is optionally replaced by one or more substituents R 4 Replacement, and

[0045] One or more non-adjacent CH2- groups are optionally R 4 C = CR 4 C≡C, Si(R) 4 )2、Ge(R 4 )2、Sn(R 4 )2. C=O, C=S, C=Se, C=NR 4 、P(=O)(R 4 SO, SO2, NR 4 O, S or CONR 4 replace;

[0046] C1-C 40 -alkoxy,

[0047] The C1-C 40 -Alkoxy group is optionally replaced by one or more substituents R 4 Replacement, and

[0048] One or more non-adjacent CH2- groups are optionally R 4 C = CR 4 C≡C, Si(R) 4 )2、Ge(R 4 )2、Sn(R4 )2. C=O, C=S, C=Se, C=NR 4 、P(=O)(R 4 SO, SO2, NR 4 O, S or CONR 4 replace;

[0049] C1-C 40 -Thioalkoxy,

[0050] The C1-C 40 -Thioalkoxy group is optionally replaced by one or more substituents R 4 Replacement, and

[0051] One or more non-adjacent CH2- groups are optionally R 4 C = CR 4 C≡C, Si(R) 4 )2、Ge(R 4 )2、Sn(R 4 )2. C=O, C=S, C=Se, C=NR 4 、P(=O)(R 4 SO, SO2, NR 4 O, S or CONR 4 replace;

[0052] C2-C 40 -Alkenyl

[0053] The C2-C 40 - The alkenyl group is optionally replaced by one or more substituents R 4 Replacement, and

[0054] One or more non-adjacent CH2- groups are optionally R 4 C = CR 4 C≡C, Si(R) 4 )2、Ge(R 4 )2、Sn(R 4 )2. C=O, C=S, C=Se, C=NR 4 、P(=O)(R 4 SO, SO2, NR 4 O, S or CONR 4 replace;

[0055] C2-C 40 -Alkyne group.

[0056] The C2-C 40 -The alkynyl group is optionally replaced by one or more substituents R. 4 Replacement, and

[0057] One or more non-adjacent CH2- groups are optionally R 4 C = CR 4 C≡C, Si(R) 4 )2、Ge(R 4 )2、Sn(R 4 )2. C=O, C=S, C=Se, C=NR 4 、P(=O)(R 4 SO, SO2, NR 4 O, S or CONR 4 replace;

[0058] C6-C 60 -Aryl

[0059] The C6-C 60 -The aryl group is optionally replaced by one or more substituents R 4 Replace; and

[0060] C3-C 57 - heteroaryl

[0061] The C3-C 57 -The heteroaryl group is optionally replaced by one or more substituents R 4 replace;

[0062] R 4 Each time it appears, independently select from the following groups:

[0063] Hydrogen, deuterium, halogens, OPh (Ph = phenyl), SPh, CF3, CN, Si(C1-C5-alkyl)3, Si(Ph)3

[0064] C1-C5-alkyl,

[0065] In this embodiment, one or more hydrogen atoms may be independently replaced by deuterium, halogen, CN or CF3;

[0066] C1-C5-alkoxy,

[0067] In this embodiment, one or more hydrogen atoms may be independently replaced by deuterium, halogen, CN or CF3;

[0068] C1-C5-thioalkoxy,

[0069] In this embodiment, one or more hydrogen atoms may be independently replaced by deuterium, halogen, CN or CF3;

[0070] C2-C5-alkenyl,

[0071] In this embodiment, one or more hydrogen atoms may be independently replaced by deuterium, halogen, CN or CF3;

[0072] C2-C5-alkynyl group,

[0073] In this embodiment, one or more hydrogen atoms may be independently replaced by deuterium, halogen, CN or CF3;

[0074] C6-C 18 -Aryl

[0075] The C6-C 18 -The aryl group is optionally replaced by one or more substituents R 5 replace;

[0076] C3-C 17 - heteroaryl

[0077] The C3-C 17 -The heteroaryl group is optionally replaced by one or more substituents R 5 replace;

[0078] N(C6-C 18 -Aryl)2,

[0079] N(C3-C 17 -heteroaryl)2; and

[0080] N(C3-C 17 -heteroaryl)(C6-C 18 -Aryl).

[0081] In one embodiment of the invention, R I R II R III R IV R V R VI R VII R VIII R IX R X and R XI Each time it appears, independently select from the following groups:

[0082] hydrogen,

[0083] Me、 i Pr、 t Bu, CN, CF3, F,

[0084] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0085] Pyridyl group, wherein the pyridyl group is optionally selected independently of one or more elements, Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0086] Carbazolyl, wherein the carbazolyl group is optionally selected independently of one or more elements Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0087] Triazine group, wherein the triazine group is optionally selected independently of one or more elements, Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0088] and N(Ph)2, wherein N(Ph)2 is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu, F, and Ph.

[0089] In one embodiment of the invention, R I R II R III R IV R V R VI R VII R VIII R IX R X and R XI Each time it appears, independently select from the following groups:

[0090] Hydrogen, Me, i Pr、 t Bu, CN, CF3, F,

[0091] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0092] Pyridyl group, wherein the pyridyl group is optionally selected independently of one or more elements, Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0093] Carbazolyl, wherein the carbazolyl group is optionally selected independently of one or more elements, Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0094] Triazine group, wherein the triazine group is optionally selected independently of one or more elements, Me, i Pr、 t Substituent substitutions in the group consisting of Bu, CN, CF3, F, and Ph.

[0095] In one embodiment of the invention, R I R II R III R IV R V R VI R VII R VIII R IX R X and R XI Each time it appears, independently select from the following groups:

[0096] Hydrogen, Me, i Pr、 t Bu, CN, CF3, F,

[0097] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu, CN, CF3, F, and Ph.

[0098] In one embodiment of the invention, R I R II R III R IV R V R VI R VII R VIII R IX R X and R XI Each time it appears, independently select from the following groups:

[0099] hydrogen,

[0100] Me、 i Pr、 t Bu, F,

[0101] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 tSubstituent substitutions in the group consisting of Bu, CN, CF3, F, and Ph.

[0102] In one embodiment of the invention, R I R II R III R IV R V R VI R VII R VIII R IX R X and R XI Each time it appears, independently select from the following groups:

[0103] hydrogen,

[0104] Me、 i Pr、 t Bu, F,

[0105] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph.

[0106] In one embodiment of the invention, R I R II R III R IV R V R VI R VII R VIII R IX R X and R XI Each time it appears, independently select from the following groups:

[0107] hydrogen,

[0108] Me、 i Pr、 t Bu,

[0109] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph.

[0110] In a preferred embodiment of the present invention, R I and R X It is hydrogen.

[0111] In one embodiment of the present invention, R I R V RVI and R X It is hydrogen.

[0112] In one embodiment of the invention, R XI Each time it appears, independently select from the following groups:

[0113] hydrogen,

[0114] Me、 i Pr、 t Bu, CN, CF3

[0115] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0116] and N(Ph)2, wherein N(Ph)2 is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu, F, and Ph.

[0117] In a preferred embodiment of the present invention, R XI Each time it appears, independently select from the following groups:

[0118] hydrogen,

[0119] Me、 i Pr、 t Bu,

[0120] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph

[0121] and N(Ph)2, wherein N(Ph)2 is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph.

[0122] In a more preferred embodiment of the present invention, R XI Each time it appears, independently select from the following groups:

[0123] Me、 i Pr、 t Bu,

[0124] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、t Substituent substitutions in the group consisting of Bu and Ph

[0125] and N(Ph)2, wherein N(Ph)2 is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph.

[0126] In one embodiment of the invention, R XI Each time it appears, independently select from the following groups:

[0127] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph

[0128] and N(Ph)2, wherein N(Ph)2 is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph.

[0129] In one embodiment of the present invention, R XI It is independent each time it appears.

[0130] N(Ph)2, wherein N(Ph)2 is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph.

[0131] In one embodiment of the invention, R XI It is N(Ph)2 independently each time it appears.

[0132] In one embodiment of the invention, R a Each time it appears, independently select from the following groups:

[0133] hydrogen,

[0134] Me、 i Pr、 t Bu, CN, CF3, F,

[0135] aryl, wherein the aryl group is optionally selected independently of one or more elements, Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0136] Pyridyl group, wherein the pyridyl group is optionally selected independently of one or more elements, Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0137] Carbazolyl, wherein the carbazolyl group is optionally selected independently of one or more elements Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0138] Triazine group, wherein the triazine group is optionally selected independently of one or more elements, Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0139] and N(Ph)2, wherein N(Ph)2 is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu, F, and Ph.

[0140] In other embodiments of the invention, R a Each time it appears, independently select from the following groups:

[0141] hydrogen,

[0142] Me、 i Pr、 t Bu, F,

[0143] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0144] Carbazolyl, wherein the carbazolyl group is optionally selected independently of one or more elements Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0145] and N(Ph)2, wherein N(Ph)2 is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu, F, and Ph.

[0146] In other embodiments of the invention, R a Each time it appears, independently select from the following groups:

[0147] hydrogen,

[0148] Me、 i Pr、 t Bu, F,

[0149] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu, F, and Ph

[0150] Carbazolyl, wherein the carbazolyl group is optionally selected independently of one or more elements, Me, i Pr、 t Substituent substitutions in the group consisting of Bu, F, and Ph

[0151] and N(Ph)2, wherein N(Ph)2 is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu, F, and Ph.

[0152] In other embodiments of the invention, R a Each time it appears, independently select from the following groups:

[0153] hydrogen,

[0154] Me、 i Pr、 t Bu,

[0155] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph

[0156] Carbazolyl, wherein the carbazolyl group is optionally selected independently of one or more elements, Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph

[0157] and N(Ph)2, wherein N(Ph)2 is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph.

[0158] In other embodiments of the invention, R a Each time it appears, independently select from the following groups:

[0159] hydrogen,

[0160] Me、 i Pr、 t Bu,

[0161] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph

[0162] and N(Ph)2, wherein N(Ph)2 is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph.

[0163] In other embodiments of the invention, R a Each time it appears, independently select from the following groups:

[0164] hydrogen,

[0165] Me、 i Pr、 t Bu,

[0166] as well as

[0167] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph.

[0168] In one embodiment of the invention, R a Each time it appears, independently select from the following groups:

[0169] hydrogen,

[0170] Ph.

[0171] In one embodiment of the invention, R a It is hydrogen each time it appears.

[0172] In a preferred embodiment of the present invention, R V =R X And R I =R VI .

[0173] In one embodiment of the invention, R 5 Each time it appears, independently select from the following groups:

[0174] hydrogen,

[0175] Me、 i Pr、 t Bu,

[0176] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph.

[0177] In one embodiment of the invention, R 5 Each time it appears, independently select from the following groups:

[0178] Hydrogen, and

[0179] Ph.

[0180] In one embodiment of the invention, R 5 It is hydrogen each time it appears.

[0181] In one embodiment of the invention, the organic molecule comprises or is composed of structures of formula II-a, II-b and II-c.

[0182]

[0183]

[0184] In this description, reference to specific structures, such as those of formulas II-a, II-b, and II-c, may be made in a general manner to the substituent R. I To R XI Those skilled in the art will understand that the formula defines certain substituents as hydrogen. In this case, only the remaining substituents may be selected from the group defined herein.

[0185] In one embodiment of the invention, the organic molecule comprises a structure according to any one of formula II-a, II-b, or II-c, or is composed of a structure according to any one of formula II-a, II-b, or II-c, wherein R I R II R III R IV R V R VI R VII R VIII R IX R X and R XI Each time it appears, independently select from the following groups:

[0186] hydrogen,

[0187] Me、 i Pr、 tBu, CN, CF3, F,

[0188] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0189] Pyridyl group, wherein the pyridyl group is optionally selected independently of one or more elements, Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0190] Carbazolyl, wherein the carbazolyl group is optionally selected independently of one or more elements Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0191] Triazine group, wherein the triazine group is optionally selected independently of one or more elements, Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0192] and N(Ph)2, wherein N(Ph)2 is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu, F, and Ph

[0193] If not defined as H in Equations II-a, II-b and II-c respectively.

[0194] In one embodiment of the invention, the organic molecule comprises a structure according to any one of formula II-a, II-b, or II-c, or is composed of a structure according to any one of formula II-a, II-b, or II-c, wherein R I R II R III R IV R V R VI R VII R VIII R IX and R X Each time it appears, independently select from the following groups:

[0195] hydrogen,

[0196] Me、 i Pr、 t Bu, CN, CF3, F,

[0197] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0198] Pyridyl group, wherein the pyridyl group is optionally selected independently of one or more elements, Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0199] Carbazolyl, wherein the carbazolyl group is optionally selected independently of one or more elements Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0200] Triazine group, wherein the triazine group is optionally selected independently of one or more elements, Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0201] If not defined as H in Equations II-a, II-b and II-c respectively.

[0202] In one embodiment of the invention, the organic molecule comprises a structure according to any one of formula II-a, II-b, or II-c, or is composed of a structure according to any one of formula II-a, II-b, or II-c, wherein R I R II R III R IV R V R VI R VII R VIII R IX and R X Each time it appears, independently select from the following groups:

[0203] hydrogen,

[0204] Me、 i Pr、 t Bu, CN, CF3, F,

[0205] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0206] If not defined as H in Equations II-a, II-b and II-c respectively.

[0207] In one embodiment of the invention, the organic molecule comprises a structure according to any one of formula II-a, II-b, or II-c, or is composed of a structure according to any one of formula II-a, II-b, or II-c, wherein R I R II R III R IV R V R VI R VII R VIII R IX and R X Each time it appears, independently select from the following groups:

[0208] hydrogen,

[0209] Me、 i Pr、 t Bu, F,

[0210] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0211] If not defined as H in Equations II-a, II-b and II-c respectively.

[0212] In one embodiment of the invention, the organic molecule comprises a structure according to any one of formula II-a, II-b, or II-c, or is composed of a structure according to any one of formula II-a, II-b, or II-c, wherein R I R II R III R IV R V R VI R VII R VIII R IX and R X Each time it appears, independently select from the following groups:

[0213] hydrogen,

[0214] Me、 i Pr、 t Bu, F,

[0215] Ph, wherein Ph is optionally selected independently of one or more Me,i Pr、 t Substituent substitutions in the group consisting of Bu and Ph

[0216] If not defined as H in Equations II-a, II-b and II-c respectively.

[0217] In one embodiment of the invention, the organic molecule comprises a structure according to any one of formula II-a, II-b, or II-c, or is composed of a structure according to any one of formula II-a, II-b, or II-c, wherein R I R II R III R IV R V R VI R VII R VIII R IX and R X Each time it appears, independently select from the following groups:

[0218] hydrogen,

[0219] Me、 i Pr、 t Bu,

[0220] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph

[0221] If not defined as H in Equations II-a, II-b and II-c respectively.

[0222] In a preferred embodiment of the invention, the organic molecule comprises a structure according to any one of formula II-a, II-b, or II-c, or is composed of a structure according to any one of formula II-a, II-b, or II-c, wherein R I and R X It is hydrogen.

[0223] In one embodiment of the invention, the organic molecule comprises a structure according to any one of formula II-a, II-b, or II-c, or is composed of a structure according to any one of formula II-a, II-b, or II-c, wherein R I R V R VI and R X It is hydrogen.

[0224] In one embodiment of the invention, the organic molecule comprises a structure according to any one of formula II-a, II-b, or II-c, or is composed of a structure according to any one of formula II-a, II-b, or II-c, wherein R XI Each time it appears, independently select from the following groups:

[0225] hydrogen,

[0226] Me、 i Pr、 t Bu, CN, CF3

[0227] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0228] and N(Ph)2, wherein N(Ph)2 is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu, F, and Ph.

[0229] In a preferred embodiment of the invention, the organic molecule comprises a structure according to any one of formula II-a, II-b, or II-c, or is composed of a structure according to any one of formula II-a, II-b, or II-c, wherein R XI Each time it appears, independently select from the following groups:

[0230] hydrogen,

[0231] Me、 i Pr、 t Bu,

[0232] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph

[0233] and N(Ph)2, wherein N(Ph)2 is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph.

[0234] In a more preferred embodiment of the invention, the organic molecule comprises a structure according to any one of formula II-a, II-b, or II-c, or is composed of a structure according to any one of formula II-a, II-b, or II-c, wherein R XIEach time it appears, independently select from the following groups:

[0235] Me、 i Pr、 t Bu,

[0236] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph

[0237] and N(Ph)2, wherein N(Ph)2 is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph.

[0238] In one embodiment of the invention, the organic molecule comprises a structure according to any one of formula II-a, II-b, or II-c, or is composed of a structure according to any one of formula II-a, II-b, or II-c, wherein R XI Each time it appears, independently select from the following groups:

[0239] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph

[0240] and N(Ph)2, wherein N(Ph)2 is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph.

[0241] In one embodiment of the invention, the organic molecule comprises a structure according to any one of formula II-a, II-b, or II-c, or is composed of a structure according to any one of formula II-a, II-b, or II-c, wherein R XI It is independent each time it appears.

[0242] N(Ph)2, wherein N(Ph)2 is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph.

[0243] In one embodiment of the invention, the organic molecule comprises a structure according to any one of formula II-a, II-b, or II-c, or is composed of a structure according to any one of formula II-a, II-b, or II-c, wherein RXI It is independent each time it appears.

[0244] N(Ph)2.

[0245] In one embodiment of the invention, the organic molecule comprises a structure according to any one of formula II-a, II-b, or II-c, or is composed of a structure according to any one of formula II-a, II-b, or II-c, wherein R a Each time it appears, independently select from the following groups:

[0246] hydrogen,

[0247] Me、 i Pr、 t Bu, CN, CF3, F,

[0248] aryl, wherein the aryl group is optionally selected independently of one or more elements, Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0249] Pyridyl group, wherein the pyridyl group is optionally selected independently of one or more elements, Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0250] Carbazolyl, wherein the carbazolyl group is optionally selected independently of one or more elements Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0251] Triazine group, wherein the triazine group is optionally selected independently of one or more elements, Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0252] and N(Ph)2, wherein N(Ph)2 is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu, F, and Ph.

[0253] In other embodiments of the invention, the organic molecule comprises a structure according to any one of formula II-a, II-b, or II-c, or is composed of a structure according to any one of formula II-a, II-b, or II-c, wherein R a Each time it appears, independently select from the following groups:

[0254] hydrogen,

[0255] Me、 i Pr、 t Bu, F,

[0256] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0257] Carbazolyl, wherein the carbazolyl group is optionally selected independently of one or more elements Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0258] and N(Ph)2, wherein N(Ph)2 is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu, F, and Ph.

[0259] In other embodiments of the invention, the organic molecule comprises a structure according to any one of formula II-a, II-b, or II-c, or is composed of a structure according to any one of formula II-a, II-b, or II-c, wherein R a Each time it appears, independently select from the following groups:

[0260] hydrogen,

[0261] Me、 i Pr、 t Bu, F,

[0262] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu, F, and Ph

[0263] Carbazolyl, wherein the carbazolyl group is optionally selected independently of one or more elements Me, i Pr、 t Substituent substitutions in the group consisting of Bu, F, and Ph

[0264] and N(Ph)2, wherein N(Ph)2 is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu, F, and Ph.

[0265] In other embodiments of the invention, the organic molecule comprises a structure according to any one of formula II-a, II-b, or II-c, or is composed of a structure according to any one of formula II-a, II-b, or II-c, wherein R a Each time it appears, independently select from the following groups:

[0266] hydrogen,

[0267] Me、 i Pr、 t Bu,

[0268] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph

[0269] Carbazolyl, wherein the carbazolyl group is optionally selected independently of one or more elements Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph

[0270] and N(Ph)2, wherein N(Ph)2 is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph.

[0271] In other embodiments of the invention, the organic molecule comprises a structure according to any one of formula II-a, II-b, or II-c, or is composed of a structure according to any one of formula II-a, II-b, or II-c, wherein R a Each time it appears, independently select from the following groups:

[0272] hydrogen,

[0273] Me、 i Pr、 t Bu,

[0274] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph

[0275] and N(Ph)2, wherein N(Ph)2 is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph.

[0276] In other embodiments of the invention, the organic molecule comprises a structure according to any one of formula II-a, II-b, or II-c, or is composed of a structure according to any one of formula II-a, II-b, or II-c, wherein R a Each time it appears, independently select from the following groups:

[0277] hydrogen,

[0278] Me、 i Pr、 t Bu,

[0279] as well as

[0280] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph.

[0281] In a preferred embodiment of the invention, the organic molecule comprises a structure according to any one of formula II-a, II-b, or II-c, or is composed of a structure according to any one of formula II-a, II-b, or II-c, wherein R V =R X And R I =R VI .

[0282] In a preferred embodiment of the invention, the organic molecule comprises or is composed of a structure of formula II-a.

[0283] In a more preferred embodiment of the invention, the organic molecule comprises or is composed of a structure of formula II-a, wherein R XI Each time it appears, independently select from the following groups:

[0284] Me、 i Pr、 t Bu,

[0285] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph

[0286] and N(Ph)2, wherein N(Ph)2 is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu, F, and Ph.

[0287] In one embodiment of the invention, the organic molecule comprises or is composed of a structure of formula II-a, wherein R XI Each time it appears, independently select from the following groups:

[0288] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph

[0289] and N(Ph)2, wherein N(Ph)2 is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph.

[0290] In one embodiment of the invention, the organic molecule comprises or is composed of a structure of formula II-a, wherein R XI It is independent each time it appears.

[0291] N(Ph)2, wherein N(Ph)2 is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph.

[0292] In one embodiment of the invention, the organic molecule comprises or is composed of a structure of formula II-a, wherein R XI It is independent each time it appears.

[0293] N(Ph)2.

[0294] In another embodiment of the invention, the organic molecule comprises or is composed of the structure of Formula III.

[0295]

[0296] In one embodiment of the invention, the organic molecule comprises or is composed of the structure of Formula III, wherein R I R II R III R IV R V R VI R VII R VIII R IX and R X Each time it appears, independently select from the following groups:

[0297] hydrogen,

[0298] Me、 i Pr、 t Bu, CN, CF3, F,

[0299] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0300] Pyridyl group, wherein the pyridyl group is optionally selected independently of one or more elements, Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0301] Carbazolyl, wherein the carbazolyl group is optionally selected independently of one or more elements Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0302] Triazine group, wherein the triazine group is optionally selected independently of one or more elements, Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0303] and N(Ph)2, wherein N(Ph)2 is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu, F, and Ph.

[0304] In one embodiment of the invention, the organic molecule comprises or is composed of the structure of Formula III, wherein R I R II R III R IV R V R VI R VII R VIII R IX and R X Each time it appears, independently select from the following groups:

[0305] hydrogen,

[0306] Me、 i Pr、 t Bu, CN, CF3, F,

[0307] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0308] Pyridyl group, wherein the pyridyl group is optionally selected independently of one or more elements, Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0309] Carbazolyl, wherein the carbazolyl group is optionally selected independently of one or more elements Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0310] Triazine group, wherein the triazine group is optionally selected independently of one or more elements, Me, i Pr、 t Substituent substitutions in the group consisting of Bu, CN, CF3, F, and Ph.

[0311] In one embodiment of the invention, the organic molecule comprises or is composed of the structure of Formula III, wherein R I R II R III R IV R V R VI R VII R VIII R IX and R X Each time it appears, independently select from the following groups:

[0312] hydrogen,

[0313] Me、 i Pr、 t Bu, CN, CF3, F,

[0314] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu, CN, CF3, F, and Ph.

[0315] In one embodiment of the invention, the organic molecule comprises or is composed of the structure of Formula III, wherein R I R II R III R IV RV R VI R VII R VIII R IX and R X Each time it appears, independently select from the following groups:

[0316] hydrogen,

[0317] Me、 i Pr、 t Bu, F,

[0318] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu, CN, CF3, F, and Ph.

[0319] In one embodiment of the invention, the organic molecule comprises or is composed of the structure of Formula III, wherein R I R II R III R IV R V R VI R VII R VIII R IX and R X Each time it appears, independently select from the following groups:

[0320] hydrogen,

[0321] Me、 i Pr、 t Bu, F,

[0322] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph.

[0323] In one embodiment of the invention, the organic molecule comprises or is composed of the structure of Formula III, wherein R I R II R III R IV R V R VI R VII R VIII R IX and R X Each time it appears, independently select from the following groups:

[0324] hydrogen,

[0325] Me、 i Pr、 t Bu,

[0326] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph.

[0327] In a preferred embodiment of the invention, the organic molecule comprises or is composed of the structure of Formula III, wherein R I and R X It is hydrogen.

[0328] In one embodiment of the invention, the organic molecule comprises or is composed of the structure of Formula III, wherein R I R V R VI and R X It is hydrogen.

[0329] In one embodiment of the invention, the organic molecule comprises or is composed of the structure of Formula III, wherein R a Each time it appears, independently select from the following groups:

[0330] hydrogen,

[0331] Me、 i Pr、 t Bu, CN, CF3, F,

[0332] aryl, wherein the aryl group is optionally selected independently of one or more elements, Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0333] Pyridyl group, wherein the pyridyl group is optionally selected independently of one or more elements, Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0334] Carbazolyl, wherein the carbazolyl group is optionally selected independently of one or more elements Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0335] Triazine group, wherein the triazine group is optionally selected independently of one or more elements, Me, i Pr、t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0336] and N(Ph)2, wherein N(Ph)2 is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu, F, and Ph.

[0337] In other embodiments of the invention, the organic molecule comprises or is composed of the structure of Formula III, wherein R a Each time it appears, independently select from the following groups:

[0338] hydrogen,

[0339] Me、 i Pr、 t Bu, F,

[0340] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0341] Carbazolyl, wherein the carbazolyl group is optionally selected independently of one or more elements Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0342] and N(Ph)2, wherein N(Ph)2 is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu, F, and Ph.

[0343] In other embodiments of the invention, the organic molecule comprises or is composed of the structure of Formula III, wherein R a Each time it appears, independently select from the following groups:

[0344] hydrogen,

[0345] Me、 i Pr、 t Bu, F,

[0346] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu, F, and Ph

[0347] Carbazolyl, wherein the carbazolyl group is optionally selected independently of one or more elements Me, i Pr、 t Substituent substitutions in the group consisting of Bu, F, and Ph

[0348] and N(Ph)2, wherein N(Ph)2 is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu, F, and Ph.

[0349] In other embodiments of the invention, the organic molecule comprises or is composed of the structure of Formula III, wherein R a Each time it appears, independently select from the following groups:

[0350] hydrogen,

[0351] Me、 i Pr、 t Bu,

[0352] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph

[0353] Carbazolyl, wherein the carbazolyl group is optionally selected independently of one or more elements Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph

[0354] and N(Ph)2, wherein N(Ph)2 is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph.

[0355] In other embodiments of the invention, the organic molecule comprises or is composed of the structure of Formula III, wherein R a Each time it appears, independently select from the following groups:

[0356] hydrogen,

[0357] Me、 i Pr、 t Bu,

[0358] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph

[0359] and N(Ph)2, wherein N(Ph)2 is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph.

[0360] In other embodiments of the invention, the organic molecule comprises or is composed of the structure of Formula III, wherein R a Each time it appears, independently select from the following groups:

[0361] hydrogen,

[0362] Me、 i Pr、 t Bu,

[0363] as well as

[0364] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph.

[0365] In a preferred embodiment of the invention, the organic molecule comprises or is composed of the structure of Formula III, wherein R V =R X And R I =R VI .

[0366] In another embodiment of the invention, the organic molecule comprises or is composed of the structure of formula IV.

[0367]

[0368] In one embodiment of the invention, the organic molecule comprises or is composed of the structure of formula IV, wherein R I R V R VI and R X Each time it appears, independently select from the following groups:

[0369] hydrogen,

[0370] Me、 i Pr、 t Bu, CN, CF3, F,

[0371] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0372] Pyridyl group, wherein the pyridyl group is optionally selected independently of one or more elements, Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0373] Carbazolyl, wherein the carbazolyl group is optionally selected independently of one or more elements Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0374] Triazine group, wherein the triazine group is optionally selected independently of one or more elements, Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0375] and N(Ph)2, wherein N(Ph)2 is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu, F, and Ph.

[0376] In one embodiment of the invention, the organic molecule comprises or is composed of the structure of formula IV, wherein R I R V R VI and R X Each time it appears, independently select from the following groups:

[0377] hydrogen,

[0378] Me、 i Pr、 t Bu, CN, CF3, F,

[0379] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0380] Pyridyl group, wherein the pyridyl group is optionally selected independently of one or more elements, Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0381] Carbazolyl, wherein the carbazolyl group is optionally selected independently of one or more elements Me, i Pr、 tSubstituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0382] Triazine group, wherein the triazine group is optionally selected independently of one or more elements, Me, i Pr、 t Substituent substitutions in the group consisting of Bu, CN, CF3, F, and Ph.

[0383] In one embodiment of the invention, the organic molecule comprises or is composed of the structure of formula IV, wherein R I R V R VI and R X Each time it appears, independently select from the following groups:

[0384] hydrogen,

[0385] Me、 i Pr、 t Bu, CN, CF3, F,

[0386] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu, CN, CF3, F, and Ph.

[0387] In one embodiment of the invention, the organic molecule comprises or is composed of the structure of formula IV, wherein R I R V R VI and R X Each time it appears, independently select from the following groups:

[0388] hydrogen,

[0389] Me、 i Pr、 t Bu, F,

[0390] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu, CN, CF3, F, and Ph.

[0391] In one embodiment of the invention, the organic molecule comprises or is composed of the structure of formula IV, wherein R I R V R VI and R X Each time it appears, independently select from the following groups:

[0392] hydrogen,

[0393] Me、 i Pr、 t Bu, F,

[0394] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph.

[0395] In one embodiment of the invention, the organic molecule comprises or is composed of the structure of formula IV, wherein R I R V R VI and R X Each time it appears, independently select from the following groups:

[0396] hydrogen,

[0397] Me、 i Pr、 t Bu,

[0398] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph.

[0399] In a preferred embodiment of the invention, the organic molecule comprises or is composed of the structure of formula IV, wherein R I and R X It is hydrogen.

[0400] In one embodiment of the invention, the organic molecule comprises or is composed of the structure of formula IV, wherein R I R V R VI and R X Each time it appears, independently select from the following groups:

[0401] Hydrogen, Me, F.

[0402] In one embodiment of the invention, the organic molecule comprises or is composed of the structure of formula IV, wherein R I and R X Each time it appears, independently select from the following groups:

[0403] Me, F.

[0404] In one embodiment of the invention, the organic molecule comprises or is composed of the structure of formula IV, wherein R aEach time it appears, independently select from the following groups:

[0405] hydrogen,

[0406] Me、 i Pr、 t Bu, CN, CF3, F,

[0407] aryl, wherein the aryl group is optionally selected independently of one or more elements, Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0408] Pyridyl group, wherein the pyridyl group is optionally selected independently of one or more elements, Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0409] Carbazolyl, wherein the carbazolyl group is optionally selected independently of one or more elements Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0410] Triazine group, wherein the triazine group is optionally selected independently of one or more elements, Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0411] and N(Ph)2, wherein N(Ph)2 is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu, F, and Ph.

[0412] In other embodiments of the invention, the organic molecule comprises or is composed of the structure of formula IV, wherein R a Each time it appears, independently select from the following groups:

[0413] hydrogen,

[0414] Me、 i Pr、 t Bu, F,

[0415] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0416] Carbazolyl, wherein the carbazolyl group is optionally selected independently of one or more elements Me, i Pr、 t Substituents in the group consisting of Bu, CN, CF3, F, and Ph.

[0417] and N(Ph)2, wherein N(Ph)2 is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu, F, and Ph.

[0418] In other embodiments of the invention, the organic molecule comprises or is composed of the structure of formula IV, wherein R a Each time it appears, independently select from the following groups:

[0419] hydrogen,

[0420] Me、 i Pr、 t Bu, F,

[0421] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu, F, and Ph

[0422] Carbazolyl, wherein the carbazolyl group is optionally selected independently of one or more elements Me, i Pr、 t Substituent substitutions in the group consisting of Bu, F, and Ph

[0423] and N(Ph)2, wherein N(Ph)2 is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu, F, and Ph.

[0424] In other embodiments of the invention, the organic molecule comprises or is composed of the structure of formula IV, wherein R a Each time it appears, independently select from the following groups:

[0425] hydrogen,

[0426] Me、 i Pr、 t Bu,

[0427] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph

[0428] Carbazolyl, wherein the carbazolyl group is optionally selected independently of one or more elements Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph

[0429] and N(Ph)2, wherein N(Ph)2 is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph.

[0430] In other embodiments of the invention, the organic molecule comprises or is composed of the structure of formula IV, wherein R a Each time it appears, independently select from the following groups:

[0431] hydrogen,

[0432] Me、 i Pr、 t Bu,

[0433] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph

[0434] and N(Ph)2, wherein N(Ph)2 is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph.

[0435] In other embodiments of the invention, the organic molecule comprises or is composed of the structure of formula IV, wherein R a Each time it appears, independently select from the following groups:

[0436] hydrogen,

[0437] Me、 i Pr、 t Bu,

[0438] as well as

[0439] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph.

[0440] In a preferred embodiment of the invention, the organic molecule comprises or is composed of the structure of formula IV, wherein RV =R X And R I =R VI .

[0441] In one embodiment of the invention, the organic molecule comprises or is composed of the structure of formula IV, wherein R a Each time it appears, independently select from the following groups:

[0442] Hydrogen, and

[0443] Ph.

[0444] In one embodiment of the invention, the organic molecule comprises or is composed of the structure of formula IV, wherein R a It is hydrogen each time it appears.

[0445] In one embodiment of the invention, the organic molecule comprises or is composed of the structure of formula IV, wherein R 5 Each time it appears, independently select from the following groups:

[0446] hydrogen,

[0447] Me、 i Pr、 t Bu, and

[0448] Ph, wherein Ph is optionally selected independently of one or more Me, i Pr、 t Substituent substitutions in the group consisting of Bu and Ph.

[0449] In one embodiment of the invention, the organic molecule comprises or is composed of the structure of formula IV, wherein R 5 Each time it appears, independently select from the following groups:

[0450] Hydrogen, and

[0451] Ph.

[0452] In one embodiment of the invention, the organic molecule comprises or is composed of the structure of formula IV, wherein R 5 It is hydrogen each time it appears.

[0453] In another embodiment of the invention, the organic molecule comprises or is composed of the structure of formula V.

[0454] Attached Figure Description

[0455] Figure 1Emission spectrum of Example 1 (2 wt%) in PMMA.

[0456] Figure 2 Emission spectrum of Example 2 (2 wt%) in PMMA.

[0457] Figure 3 Emission spectrum of Example 3 (2 wt%) in PMMA.

[0458] Figure 4 Emission spectrum of Example 4 (2 wt%) in PMMA.

[0459] Figure 5 Emission spectrum of Example 5 (2 wt%) in PMMA. Detailed Implementation

[0460] As used throughout this application, the term "cyclic group" may be understood in the broadest sense as any monocyclic, bicyclic, or polycyclic part.

[0461] As used throughout this application, the terms “ring” and “ring system” may be understood in the broadest sense as any single-ring, double-ring, or multi-ring component.

[0462] As used throughout this application, the term "carbocyclic" in its broadest sense can be understood as any cyclic group in which the cyclic core structure comprises only carbon atoms, which may of course be substituted with hydrogen or any other substituent as defined in specific embodiments of the invention. It should be understood that the term "carbocyclic" as an adjective refers to a cyclic group in which the cyclic core structure comprises only carbon atoms, which may of course be substituted with hydrogen or any other substituent as defined in specific embodiments of the invention.

[0463] As used throughout this application, the term "heterocyclic" in its broadest sense can be understood as any cyclic group in which the cyclic core structure comprises not only carbon atoms but also at least one heteroatom. It should be understood that the term "heterocyclic" as an adjective refers to a cyclic group in which the cyclic core structure comprises not only carbon atoms but also at least one heteroatom. Unless otherwise stated in the specific embodiments, the heteroatom may be the same or different each time it appears and is independently selected from the group consisting of N, O, S, and Se. In the context of this invention, all carbon atoms or heteroatoms contained in a heterocyclic ring may, of course, be substituted with hydrogen or any other substituent as defined in the specific embodiments of this invention.

[0464] As used throughout this application, the term "aromatic ring system" may be understood in its broadest sense as any bicyclic or polycyclic aromatic component.

[0465] As used throughout this application, the term "heterocyclic aromatic system" may be understood in the broadest sense as any bicyclic or polycyclic heterocyclic aromatic moiety.

[0466] As used throughout this application, the term "fused" when referring to an aromatic or heteroaromatic ring system means that the "fused" aromatic or heteroaromatic rings share at least one bond, which is part of two ring systems. For example, in the context of this invention, naphthalene (or naphthyl as a substituent) or benzothiophene (or benzothiophene as a substituent) is considered a fused aromatic ring system in which two benzene rings (for naphthalene) or thiophene and benzene (for benzothiophene) share a bond. It should also be understood that sharing a bond in this context includes sharing two atoms constituting the respective bond, and a fused aromatic or heteroaromatic ring system can be understood as a single aromatic or heteroaromatic system. Furthermore, it should be understood that more than one bond can be shared by the aromatic or heteroaromatic rings constituting the fused aromatic or heteroaromatic ring system (e.g., in pyrene). Furthermore, it should be understood that aliphatic ring systems can also be fused, and this has the same meaning as aromatic or heteroaromatic ring systems, except that fused aliphatic ring systems are not aromatic.

[0467] As used throughout this application, the terms "aryl" and "aromatic" can be understood in the broadest sense as any monocyclic, bicyclic, or polycyclic aromatic moiety. Thus, an aryl group contains 6 to 60 aromatic ring atoms, and a heteroaryl group contains 5 to 60 aromatic ring atoms, at least one of which is a heteroatom. Nevertheless, throughout the application, the number of aromatic ring atoms may be given by subscript numbers in the definitions of certain substituents. Specifically, a heteroaromatic ring includes 1 to 3 heteroatoms. Furthermore, the terms "heteroaryl" and "heteroaromatic" can be understood in the broadest sense as any monocyclic, bicyclic, or polycyclic heteroaromatic moiety including at least one heteroatom. Unless otherwise stated in the specific embodiments, the heteroatom may be the same or different each time it appears and is independently selected from the group consisting of N, O, S, and Se. Thus, the term "arylene" refers to a divalent substituent having two binding sites with other molecular structures and thus serving as a linker structure. If the group in the exemplary embodiments is defined differently from the definition given herein, for example, if the number of aromatic ring atoms or heteroatoms differs from the given definition, the definition in the exemplary embodiments shall apply. According to the invention, a fused (cyclized) aromatic or heteroaromatic polycyclic ring consists of two or more individual aromatic or heteroaromatic rings that form a polycyclic ring via a condensation reaction.

[0468] Specifically, as used throughout this application, the terms "aryl group" or "heteroaryl group" include groups that can be bonded at any position via aromatic or heteroaromatic groups derived from benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, etc. Perylene, fluoranthene, benzo[a]anthene, benzo[a]phenanthrene, tetraphenyl, pentaphenyl, benzo[a]pyrene, furan, benzo[a]furan, isobenzo[a]furan, dibenzo[a]furan, thiophene, benzo[a]thiophene, isobenzo[a]thiophene, dibenzo[a]thiophene, selenophene, benzo[a]selenophene, isobenzo[a]selenophene, dibenzo[a]selenophene; pyrrole, indole, isoindole, carbazole, indole[a]carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenothiazine, pyrazole, indazole, imidazole, benzimidazole, naphthiazole, phenanthrimidazole, pyridinium pyridimazole, pyrazinium pyridimazole The following are compounds: azole, quinoxaline imidazole, oxazole, benzoxazole, naphthoxazole, anthraxazole, phenanthoxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, 1,3,5-triazine, quinoxaline, pyrazine, phenazine, naphthidine, 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-tetraazine, purine, pteridine, indazine, and benzothiadiazole, or combinations thereof.

[0469] As used throughout this application, the term "aliphatic" may be understood in the broadest sense when referring to ring systems, and means that the rings constituting the ring system are not aromatic or heteroaromatic rings. It should be understood that such an aliphatic ring system may be fused with one or more aromatic rings such that some (but not all) of the carbon atoms or heteroatoms in the core structure of the aliphatic ring system are part of the attached aromatic ring.

[0470] As used above and herein, the term "alkyl group" may be understood in the broadest sense as any straight-chain, branched, or cyclic alkyl substituent. In particular, the term alkyl includes substituents such as methyl (Me), ethyl (Et), and n-propyl (...). n Pr), isopropyl ( i Pr), cyclopropyl, n-butyl ( n Bu), isobutyl ( i Bu), sec-butyl ( s Bu), tert-butyl ( tBu), cyclobutyl, 2-methylbutyl, n-pentyl, secondary pentyl, tert-pentyl, 2-pentyl, neopentyl, cyclopentyl, n-hexyl, secondary hexyl, tert-hexyl, 2-hexyl, 3-hexyl, neohexyl, cyclohexyl, 1-methylcyclopentyl, 2-methylpentyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, cycloheptyl, 1-methylcyclohexyl, n-octyl, 2-ethylhexyl, cyclooctyl, 1- Bicyclo[2,2,2]octyl, 2-bicyclo[2,2,2]-octyl, 2-(2,6-dimethyl)octyl, 3-(3,7-dimethyl)octyl, adamantyl, 2,2,2-trifluoroethyl, 1,1-dimethyl-n-hexyl-1-yl, 1,1-dimethyl-n-heptyl-1-yl, 1,1-dimethyl-n-octyl-1-yl, 1,1-dimethyl-n-decyl-1-yl, 1,1 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-hexyl-1-yl, 1,1-Diethyl-n-heptyl-1-yl, 1,1-Diethyl-n-octyl-1-yl, 1,1-Diethyl-n-decyl-1-yl, 1,1-Diethyl-n-n- Dodecyl-1-yl, 1,1-diethyl-tetradecyl-1-yl, 1,1-diethyl-hexadecyl-1-yl, 1,1-diethyl-octadecyl-1-yl, 1-(n-propyl)-cyclohexyl-1-yl, 1-(n-butyl)-cyclohexyl-1-yl, 1-(n-hexyl)-cyclohexyl-1-yl, 1-(n-octyl)-cyclohexyl-1-yl and 1-(n-decyl)-cyclohexyl-1-yl.

[0471] As used above and herein, the term "alkenyl" includes straight-chain, branched, and cyclic alkenyl substituents. Exemplary examples of the term alkenyl group include substituents vinyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, or cyclooctadienyl.

[0472] As used above and herein, the term "alkynyl" includes straight-chain, branched, and cyclic alkynyl substituents. Exemplary examples of the term alkynyl group include ethynyl, propynyl, butynyl, pentyynyl, hexynyl, heptyynyl, or octyynyl.

[0473] As used above and herein, the term "alkoxy" includes straight-chain, branched, and cyclic alkoxy substituents. Exemplary examples of the term alkoxy group include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, and 2-methylbutoxy.

[0474] As used above and herein, the term "thioalkoxy" includes straight-chain, branched, and cyclic thioalkoxy substituents, wherein the O of the exemplary alkoxy group is replaced by S.

[0475] As used above and in this document, the terms “halogen” and “halogenated” can be understood in the broadest sense as preferably fluorine, chlorine, bromine or iodine.

[0476] It should be understood that when a molecular segment is described as a substituent or otherwise attached to another part, its name may be written as if it were a segment (e.g., naphthyl, dibenzofuranyl) or as if it were a whole molecule (e.g., naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or attached segments are considered equivalent.

[0477] All hydrogen atoms (H) contained in any structure mentioned herein may be replaced by deuterium (D) each time they appear, independently of each other, unless otherwise specified. Substituting hydrogen with deuterium is a common practice and will be apparent to those skilled in the art. Therefore, there are many known methods that can achieve this, and several review articles describe them (see, for example: A. Michelotti, M. Roche, Synthesis 2019, 51(06), 1319–1328, DOI:10.1055 / s-0037-1610405; J. Atzrodt, V. Derdau, T. Fey, J. Zimmermann, Angew. Chem. Int. Ed. 2007, 46(15), 7744–7765, DOI:10.1002 / anie.200700039; Y. Sawama, Y. Monguchi, H. Sajiki, Synlett 2012, 23(7), 959–972, DOI:10.1055 / s-0031-1289696).

[0478] The excited-state lifetime consists of multiple components. For example, in the case of a TADF emitter, it consists of transient fluorescence, typically on the order of nanoseconds, and delayed fluorescence, typically on the order of microseconds. Since the delayed fluorescence is three orders of magnitude larger, the transient fluorescence is insignificant, meaning that the excited-state lifetime can be estimated by the lifetime of the delayed fluorescence.

[0479] In one embodiment, the organic molecules according to the invention have an excited-state lifetime of not more than 10 μs, not more than 8 μs, especially not more than 6 μs, more preferably not more than 5 μs or not more than 4 μs, and even more preferably not more than 3 μs in a poly(methyl methacrylate) (PMMA) film having 1-5 wt% or more, particularly 2 wt% of organic molecules at room temperature (i.e., about 25 °C).

[0480] In one embodiment of the invention, the organic molecule according to the invention represents a thermally activated delayed fluorescence (TADF) emitter exhibiting a fluorescence emission frequency of less than 5000 cm⁻¹. -1 Preferred size is less than 3000cm-1 More preferably, less than 1500cm -1 Even more preferred is less than 1000cm -1 or even less than 500cm -1 ΔE ST The value, the ΔE ST The value corresponds to the energy difference between the first excited singlet state (S1) and the first excited triplet state (T1).

[0481] In other embodiments, the organic molecules according to the invention have excited-state lifetimes of no more than 10 μs, no more than 8 μs, especially no more than 6 μs, more preferably no more than 5 μs or no more than 4 μs, and even more preferably no more than 3 μs in a poly(methyl methacrylate) (PMMA) film having 1-5 wt% or more, particularly 2 wt% of organic molecules, at room temperature (i.e., about 25°C). The full width at half maximum (FWHM) is less than 0.23 eV, preferably less than 0.20 eV, more preferably less than 0.19 eV, and even more preferably less than 0.15 eV or even less than 0.12 eV.

[0482] Unless otherwise stated, in the context of organic molecules according to the invention, the excited-state lifetime is equal to or determined by the delayed fluorescence lifetime or delayed fluorescence decay time.

[0483] In other embodiments of the invention, the organic molecules according to the invention have emission peaks in the visible or near-ultraviolet range, i.e., in the wavelength range of 380 nm to 800 nm, in a poly(methyl methacrylate) (PMMA) film having 2% by weight of the organic molecules at room temperature, wherein the full width at half maximum (FWHM) is less than 0.23 eV, preferably less than 0.20 eV, more preferably less than 0.19 eV, even more preferably less than 0.15 eV, or even less than 0.12 eV.

[0484] Orbital and excited-state energies can be determined experimentally or through calculations using quantum chemical methods, particularly density functional theory. The highest occupied molecular orbital energy is E0. HOMO The energy was determined by cyclic voltammetry with an accuracy of 0.1 eV using methods known to those skilled in the art. The lowest unoccupied molecular orbital E LUMO The energy was determined as the starting point of the absorption spectrum.

[0485] The start of the absorption spectrum is determined by calculating the intersection of the tangent to the absorption spectrum with the x-axis. The tangent to the absorption spectrum is set on the low-energy side of the absorption band, at the point at half-peak of the maximum intensity of the absorption spectrum.

[0486] Unless otherwise stated, the energy of the first excited triplet state T1 is determined by the start of the phosphorescence spectrum (steady-state spectrum; a film of PMMA with 2% by weight emitter) at 77 K.

[0487] Unless otherwise stated, the energy of the first excited singlet state S1 is determined by the start of the fluorescence spectrum at room temperature (i.e., about 25°C; steady-state spectrum; a film of PMMA with 2% by weight of emitter).

[0488] The start of the emission spectrum is determined by calculating the intersection of the tangent to the emission spectrum with the x-axis. The tangent to the emission spectrum is set on the high-energy side of the emission band, at the point at half-peak of the maximum intensity of the emission spectrum.

[0489] ΔE corresponds to the energy difference between the first excited singlet state (S1) and the first excited triplet state (T1). ST The value is determined based on the first excited singlet state energy and the first excited triplet state energy as described above.

[0490] Other aspects of the invention relate to the use of the organic molecules according to the invention as light emitters or absorbers in optoelectronic devices, and / or as host materials and / or as electron transport materials, and / or as hole injection materials, and / or as hole blocking materials.

[0491] Optoelectronic devices can be understood in the broadest sense as any device based on organic materials suitable for emitting light in the visible or near-ultraviolet (UV) range, i.e., wavelengths from 380 nm to 800 nm. More preferably, optoelectronic devices are capable of emitting light in the visible range, i.e., from 400 nm to 800 nm.

[0492] In the context of this application, optoelectronic devices are more specifically selected from the group consisting of:

[0493] Organic light-emitting diodes (OLEDs),

[0494] • Photoluminescent electrochemical cells

[0495] OLED sensors, especially in gas and vapor sensors that are not hermetically shielded from external elements,

[0496] Organic diodes

[0497] Organic solar cells,

[0498] Organic transistors,

[0499] • Organic field-effect transistor,

[0500] Organic lasers, and

[0501] Down-conversion element.

[0502] The luminescent electrochemical cell comprises three layers: a cathode, an anode, and an active layer containing organic molecules according to the present invention.

[0503] In a preferred embodiment within the context of this application, the optoelectronic device is a device selected from the group consisting of organic light-emitting diodes (OLEDs), light-emitting electrochemical cells (LECs), organic lasers, and light-emitting transistors.

[0504] In one embodiment, the light-emitting layer of the organic light-emitting diode contains organic molecules according to the present invention.

[0505] In one embodiment, the light-emitting layer of the organic light-emitting diode not only contains the organic molecule according to the invention, but also contains a host material whose triplet (T1) and singlet (S1) energy levels are energies higher than those of the triplet (T1) and singlet (S1) energy levels of the organic molecule.

[0506] Other aspects of the invention relate to compositions comprising or consisting of the following:

[0507] (a) The organic molecules of the present invention, particularly in the form of emitters and / or hosts, and

[0508] (b) One or more emitters and / or host materials different from the organic molecules of the present invention, and

[0509] (c) Optionally, one or more dyes and / or one or more solvents.

[0510] In other embodiments of the invention, the composition has a photoluminescence quantum yield (PLQY) of greater than 10%, preferably greater than 20%, more preferably greater than 40%, even more preferably greater than 60% or even greater than 70% at room temperature.

[0511] Composition having at least one other emitter

[0512] One embodiment of the present invention relates to a composition comprising or consisting of the following:

[0513] (i) 1-50% by weight, preferably 5-40% by weight, particularly 10-30% by weight of the organic molecules according to the invention;

[0514] (ii) 5-98 wt%, preferably 30-93.9 wt%, particularly 40-88 wt% of a main compound H;

[0515] (iii) 1-30% by weight, particularly 1-20% by weight, preferably 1-5% by weight, of at least one other emitter molecule F, whose structure differs from that of the organic molecule according to the invention; and

[0516] (iv) optionally 0-94 wt%, preferably 0.1-65 wt%, particularly 1-50 wt%, of at least one other main compound D, the structure of which differs from the structure of the organic molecule according to the invention; and

[0517] (v) optionally 0-94% by weight, preferably 0-65% by weight, particularly 0-50% by weight of solvent.

[0518] Select components or compositions such that the total weight of the components is 100%.

[0519] In other embodiments of the invention, the composition has an emission peak in the visible light or near ultraviolet range, i.e., in the wavelength range of 380 nm to 800 nm.

[0520] In one embodiment of the invention, at least one other emitter molecule F is a purely organic emitter.

[0521] In one embodiment of the invention, at least one other emitter molecule F is a pure organic TADF emitter. Pure organic TADF emitters are known from the prior art, for example, by Wong and Zysman-Colman (“Purely Organic ThermallyActivated Delayed Fluorescence Materials for Organic Light-Emitting Diodes”, Adv. Mater. 2017, 29(22), 1605444–1605498, DOI:10.1002 / adma.201605444).

[0522] In one embodiment of the invention, at least one other emitter molecule F is a fluorescent emitter, particularly a blue, green, yellow, or red fluorescent emitter.

[0523] In other embodiments of the invention, the composition containing at least one other emitter molecule F exhibits an emission peak at room temperature in the visible or near-ultraviolet range, i.e., in the wavelength range of 380 nm to 800 nm, with a full width at half maximum (FWHM) of less than 0.30 eV, particularly less than 0.25 eV, preferably less than 0.22 eV, more preferably less than 0.19 eV, or even less than 0.17 eV, with a lower limit of 0.05 eV.

[0524] Composition in which at least one other emitter molecule F is a green fluorescent emitter

[0525] In other embodiments of the invention, at least one other emitter molecule F is a fluorescent emitter, particularly a green fluorescent emitter.

[0526] In one embodiment, at least one other emitter molecule F is a fluorescent emitter selected from the group consisting of:

[0527]

[0528]

[0529] In other embodiments of the invention, the composition has an emission peak in the visible or near-ultraviolet range, i.e., in the wavelength range of 380 nm to 800 nm, particularly 485 nm to 590 nm, preferably 505 nm to 565 nm, and even more preferably 515 nm to 545 nm. The composition in which at least one other emitting molecule F is a red fluorescent emitting element is also included.

[0530] In other embodiments of the invention, at least one other emitter molecule F is a fluorescent emitter, particularly a red fluorescent emitter.

[0531] In one embodiment, at least one other emitter molecule F is a fluorescent emitter selected from the group consisting of:

[0532]

[0533]

[0534] In other embodiments of the invention, the composition has an emission peak in the visible light or near ultraviolet range, i.e., in the wavelength range of 380 nm to 800 nm, particularly in the wavelength range of 590 nm to 690 nm, preferably in the wavelength range of 610 nm to 665 nm, and even more preferably in the wavelength range of 620 nm to 640 nm.

[0535] Eluminating layer EML

[0536] In one embodiment, the light-emitting layer (EML) of the organic light-emitting diode of the present invention comprises (or is substantially composed of) a composition comprising or consisting of the following:

[0537] (i) 1-50% by weight, preferably 5-40% by weight, particularly 10-30% by weight, of one or more organic molecules according to the invention;

[0538] (ii) at least one main compound H, comprising 5-99% by weight, preferably 30-94.9% by weight, and particularly 40-89% by weight; and

[0539] (iii) optionally 0-94 wt%, preferably 0.1-65 wt%, particularly 1-50 wt%, of at least one other main compound D, the structure of which differs from the structure of the organic molecule according to the invention; and

[0540] (iv) optional 0-94% by weight, preferably 0-65% by weight, particularly 0-50% by weight of solvent; and

[0541] (v) Optional 0-30% by weight, particularly 0-20% by weight, preferably 0-5% by weight, of at least one other emitter molecule F, the structure of which differs from the structure of the organic molecule according to the invention.

[0542] Preferably, energy can be transferred from the host compound H to one or more organic molecules of the present invention, particularly from the first excited triplet state T1(H) of the host compound H to the first excited triplet state T1(E) of one or more organic molecules of the present invention and / or from the first excited singlet state S1(H) of the host compound H to the first excited singlet state S1(E) of one or more organic molecules of the present invention.

[0543] In one embodiment, the host compound H has an energy E containing -5 eV to -6.5 eV. HOMO The highest occupied molecular orbital (H) of (H) is HOMO(H), and an organic molecule E according to the present invention has energy E HOMO The highest occupied molecular orbital HOMO(E) of (E) is shown in the figure. HOMO (H)>E HOMO (E).

[0544] In other embodiments, the host compound H has energy E. LUMO The lowest unoccupied molecular orbital LUMO(H) of (H), and an organic molecule E according to the invention having energy E LUMO The lowest unoccupied molecular orbital LUMO(E) of (E), where E LUMO (H)>E LUMO (E).

[0545] EML containing at least one other host compound D

[0546] In other embodiments, the light-emitting layer (EML) of the organic light-emitting diode of the present invention comprises (or is substantially composed of) a composition comprising or consisting of the following:

[0547] (i) 1-50% by weight, preferably 5-40% by weight, particularly 10-30% by weight of an organic molecule according to the invention;

[0548] (ii) 5-99 wt%, preferably 30-94.9 wt%, particularly 40-89 wt% of a main compound H; and

[0549] (iii) 0-94 wt%, preferably 0.1-65 wt%, particularly 1-50 wt%, of at least one other host compound D, whose structure differs from that of the organic molecule according to the invention; and

[0550] (iv) optional 0-94% by weight, preferably 0-65% by weight, particularly 0-50% by weight of solvent; and

[0551] (v) Optional 0-30% by weight, particularly 0-20% by weight, preferably 0-5% by weight, of at least one other emitter molecule F, the structure of which differs from the structure of the organic molecule according to the invention.

[0552] In one embodiment of the organic light-emitting diode of the present invention, the host compound H has an energy E containing -5 eV to -6.5 eV. HOMO The highest occupied molecular orbital of (H) is HOMO(H), and at least one other host compound D has an energy E HOMO The highest occupied molecular orbital HOMO(D) of (D) is E HOMO (H)>E HOMO (D). Relationship E HOMO (H)>E HOMO (D) It facilitates efficient hole transport.

[0553] In other embodiments, the host compound H has energy E. LUMO The lowest unoccupied molecular orbital LUMO(H) of (H), and at least one other host compound D has an energy E LUMO The lowest unoccupied molecular orbital LUMO(D) of (D), where E LUMO (H)>E LUMO (D). Relationship E LUMO (H)>E LUMO (D) It contributes to efficient electronic transmission.

[0554] In one embodiment of the organic light-emitting diode of the present invention, the host compound H has energy E. HOMO The highest occupied molecular orbital (HOMO) of (H) and the energy E LUMO The lowest unoccupied molecular orbital LUMO(H) of (H), and

[0555] At least one other host compound D has energy E HOMO The highest occupied molecular orbital (HOMO) of (D) and the energy E LUMOThe lowest unoccupied molecular orbital LUMO(D) of (D),

[0556] The organic molecule E of the present invention has energy E HOMO The highest occupied molecular orbital (HOMO) of (E) and the energy E LUMO The lowest unoccupied molecular orbital LUMO(E) of (E),

[0557] in

[0558] E HOMO (H)>E HOMO (D) and the energy level (E) of the highest occupied molecular orbital HOMO(E) of the organic molecule according to the present invention. HOMO (E)) and the energy level of the highest occupied molecular orbital HOMO(H) of the host compound H (E) HOMO The difference between (H) is -0.5 eV to 0.5 eV, more preferably -0.3 eV to 0.3 eV, even more preferably -0.2 eV to 0.2 eV or even -0.1 eV to 0.1 eV; and

[0559] E LUMO (H)>E LUMO (D) and the energy level (E) of the lowest unoccupied molecular orbital LUMO (E) of the organic molecule according to the invention. LUMO (E)) and the energy level (E) of the lowest unoccupied molecular orbital LUMO(D) of at least one other host compound D. LUMO The difference between (D) is -0.5eV to 0.5eV, more preferably -0.3eV to 0.3eV, even more preferably -0.2eV to 0.2eV or even -0.1eV to 0.1eV.

[0560] EML containing at least one other emitter molecule F

[0561] In other embodiments, the light-emitting layer EML comprises (or is substantially composed of) a composition comprising or consisting of the following:

[0562] (i) 1-50% by weight, preferably 5-40% by weight, particularly 10-30% by weight of an organic molecule according to the invention;

[0563] (ii) 5-98 wt%, preferably 30-93.9 wt%, particularly 40-88 wt% of a main compound H;

[0564] (iii) 1-30% by weight, particularly 1-20% by weight, preferably 1-5% by weight, of at least one other emitter molecule F, whose structure differs from that of the organic molecule according to the invention; and

[0565] (iv) optionally 0-94 wt%, preferably 0.1-65 wt%, particularly 1-50 wt%, of at least one other main compound D, the structure of which differs from the structure of the organic molecule according to the invention; and

[0566] (v) optionally 0-94% by weight, preferably 0-65% by weight, particularly 0-50% by weight of solvent.

[0567] In other embodiments, the luminescent layer EML comprises (or is substantially composed of) a composition as described in compositions having at least one other emitter, wherein the at least one other emitter molecule F is defined in compositions wherein the at least one other emitter molecule F is a green fluorescent emitter.

[0568] In other embodiments, the luminescent layer EML comprises (or is substantially composed of) a composition as described in compositions having at least one other emitter, wherein the at least one other emitter molecule F is defined in compositions wherein the at least one other emitter molecule F is a red fluorescent emitter.

[0569] In one embodiment of the luminescent layer EML containing at least one other emitter molecule F, energy can be transferred from one or more organic molecules E of the present invention to at least one other emitter molecule F, particularly from the first excited singlet state S1(E) of one or more organic molecules E of the present invention to the first excited singlet state S1(F) of at least one other emitter molecule F.

[0570] In one embodiment, the first excited singlet state S1(H) of a host compound H of the luminescent layer has an energy higher than that of the first excited singlet state S1(E) of one or more organic molecules E of the present invention: S1(H)>S1(E), and the first excited singlet state S1(H) of a host compound H has an energy higher than that of the first excited singlet state S1(F) of at least one other emitter molecule F: S1(H)>S1(F).

[0571] In one embodiment, the first excited triplet state T1(H) of a host compound H has an energy higher than the first excited triplet state T1(E) of one or more organic molecules E of the present invention: T1(H)>T1(E), and the first excited triplet state T1(H) of a host compound H has an energy higher than the first excited triplet state T1(F) of at least one other emitter molecule F: T1(H)>T1(F).

[0572] In one embodiment, the first excited singlet state S1(E) of one or more organic molecules E of the present invention is higher in energy than the first excited singlet state S1(F) of at least one other emitter molecule F: S1(E)>S1(F).

[0573] In one embodiment, the first excited triplet state T1(E) of one or more organic molecules E of the present invention is higher in energy than the first excited triplet state T1(F) of at least one other emitter molecule F: T1(E)>T1(F).

[0574] In one embodiment, the first excited triplet state T1(E) of one or more organic molecules E of the present invention is higher in energy than the first excited triplet state T1(F) of at least one other emitter molecule F: T1(E)>T1(F), wherein the absolute value of the energy difference between T1(E) and T1(F) is greater than 0.3 eV, preferably greater than 0.4 eV, or even greater than 0.5 eV.

[0575] In one embodiment, the host compound H has an energy E containing -5 eV to -6.5 eV. HOMO The highest occupied molecular orbital of (H) is HOMO(H), and at least one other host compound D has an energy E HOMO The highest occupied molecular orbital HOMO(D) of (D) is E HOMO (H)>E HOMO (D)

[0576] In other embodiments, the host compound H has energy E. LUMO The lowest unoccupied molecular orbital LUMO(H) of (H), and at least one other host compound D has an energy E LUMO The lowest unoccupied molecular orbital LUMO(D) of (D), where E LUMO (H)>E LUMO (D)

[0577] In one embodiment, the host compound H has energy E. HOMO The highest occupied molecular orbital (HOMO) of (H) and the energy E LUMO The lowest unoccupied molecular orbital LUMO(H) of (H), and

[0578] At least one other host compound D has energy E HOMO The highest occupied molecular orbital (HOMO) of (D) and the energy E LUMO The lowest unoccupied molecular orbital LUMO(D) of (D),

[0579] The organic molecule E according to the present invention has energy EHOMO The highest occupied molecular orbital (HOMO) of (E) and the energy E LUMO The lowest unoccupied molecular orbital LUMO(E) of (E),

[0580] in

[0581] E HOMO (H)>E HOMO (D) and according to the invention, the energy level (E) of the highest occupied molecular orbital HOMO(E) of the organic molecule E. HOMO (E)) and the energy level of the highest occupied molecular orbital HOMO(H) of the host compound H (E) HOMO The difference between (H) is -0.5 eV to 0.5 eV, more preferably -0.3 eV to 0.3 eV, even more preferably -0.2 eV to 0.2 eV or even -0.1 eV to 0.1 eV; and E LUMO (H)>E LUMO (D) and the energy level (E) of the lowest unoccupied molecular orbital LUMO(E) of the organic molecule E according to the invention. LUMO (E)) and the energy level (E) of the lowest unoccupied molecular orbital LUMO(D) of at least one other host compound D. LUMO The difference between (D) is -0.5eV to 0.5eV, more preferably -0.3eV to 0.3eV, even more preferably -0.2eV to 0.2eV or even -0.1eV to 0.1eV.

[0582] In one embodiment of the invention, host compound D and / or host compound H are thermally activated delayed fluorescence (TADF) materials. TADF materials exhibit fluorescence spectroscopy (FSS) of less than 2500 cm⁻¹. -1 ΔE ST The value, the ΔE ST The value corresponds to the energy difference between the first excited singlet state (S1) and the first excited triplet state (T1). Preferably, the TADF material exhibits an energy difference of less than 3000 cm⁻¹. -1 More preferably, less than 1500cm -1 Even more preferred is less than 1000cm -1 or even less than 500cm -1 ΔE ST value.

[0583] In one embodiment, host compound D is a TADF material, and host compound H exhibits a length greater than 2500 cm⁻¹. -1 ΔE STValue. In a specific implementation, the host compound D is a TADF material, and the host compound H is selected from the group consisting of CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(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.

[0584] In one embodiment, the host compound H is a TADF material, and the host compound D exhibits a length greater than 2500 cm⁻¹. -1 ΔE ST Value. In a specific embodiment, the host compound H is a TADF material and the host compound D is selected from the group consisting of T2T (2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine), T3T (2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine) and / or TST (2,4,6-tris(9,9'-spirodifluorene-2-yl)-1,3,5-triazine).

[0585] In other respects, the present invention relates to optoelectronic devices comprising organic molecules or compositions of the type described herein, and more specifically, to devices selected from the group consisting of organic light-emitting diodes (OLEDs), light-emitting electrochemical cells, OLED sensors, more specifically gas and vapor sensors without hermetically shielded external surfaces, organic diodes, organic solar cells, organic transistors, organic field-effect transistors, organic lasers, and down-conversion elements.

[0586] In a preferred embodiment, the optoelectronic device is a device selected from the group consisting of organic light-emitting diodes (OLEDs), light-emitting electrochemical cells (LECs), and light-emitting transistors.

[0587] In one embodiment of the optoelectronic device of the present invention, the organic molecule E according to the present invention is used as the emitting material in the light-emitting layer EML.

[0588] In one embodiment of the optoelectronic device of the present invention, the light-emitting layer EML is composed of the composition of the present invention as described herein.

[0589] When the optoelectronic device is an OLED, it can have, for example, the following layer structure:

[0590] 1. Substrate

[0591] 2. Anode, A

[0592] 3. Hole injection layer, HIL

[0593] 4. Hole transport layer, HTL

[0594] 5. Electron blocking layer, EBL

[0595] 6. Emissive layer, EML

[0596] 7. Hole blocking layer, HBL

[0597] 8. Electronic Transport Layer (ETL)

[0598] 9. Electron Injection Layer (EIL)

[0599] 10. Cathode, C

[0600] OLEDs may optionally include only each of the layers selected from the group consisting of HIL, HTL, EBL, HBL, ETL, and EIL. Different layers may be combined, and an OLED may include more than one layer of each of the above-defined layer types.

[0601] Furthermore, in one embodiment, the optoelectronic device may include one or more protective layers that protect the device from damage caused by exposure to harmful substances in the environment, including, for example, moisture, vapor and / or gases.

[0602] In one embodiment of the invention, the optoelectronic device is an OLED having the following inverted layer structure:

[0603] 1. Substrate

[0604] 2. Cathode, C

[0605] 3. Electron Injection Layer (EIL)

[0606] 4. Electronic Transport Layer (ETL)

[0607] 5. Hole blocking layer, HBL

[0608] 6. Emissive layer, EML

[0609] 7. Electron blocking layer, EBL

[0610] 8. Hole transport layer, HTL

[0611] 9. Hole injection layer, HIL

[0612] 10. Anode, A

[0613] OLEDs may optionally include only each of the layers selected from the group consisting of HIL, HTL, EBL, HBL, ETL, and EIL. Different layers may be combined, and an OLED may include more than one layer of each of the above-defined layer types.

[0614] In one embodiment of the invention, the optoelectronic device is an OLED, which may have a stacked structure. In this structure, contrary to a typical arrangement in which OLEDs are placed side by side, the individual units are stacked on top of each other. OLEDs exhibiting a stacked structure can be used to generate mixed light, particularly white light can be generated by stacking blue, green, and red OLEDs. Furthermore, OLEDs exhibiting a stacked structure may include a charge-generating layer (CGL), which is typically located between two OLED sub-units and typically consists of an n-doped layer and a p-doped layer, with the n-doped layer of one CGL typically located closer to the anode.

[0615] In one embodiment of the invention, the optoelectronic device is an OLED, which includes two or more light-emitting layers between an anode and a cathode. Specifically, this so-called tandem OLED includes three light-emitting layers, one emitting red light, one emitting green light, and one emitting blue light, and optionally may include other layers, such as charge-generating layers, blocking layers, or transport layers between the respective light-emitting layers. In other embodiments, the light-emitting layers are stacked adjacent to each other. In other embodiments, the tandem OLED includes a charge-generating layer between every two light-emitting layers. Furthermore, adjacent light-emitting layers or light-emitting layers separated by charge-generating layers may be combined.

[0616] The substrate can be formed from any material or combination of materials. Most commonly, a glass sheet is used as the substrate. Alternatively, a thin metal layer (e.g., a copper, gold, silver, or aluminum film) or a plastic film or sheet can be used. This allows for a higher degree of flexibility. The anode A is primarily composed of a material that allows for a (substantially) transparent film. Since at least one of the two electrodes should be (substantially) transparent to allow light emission from the OLED, either the anode A or the cathode C is transparent. Preferably, the anode A contains a large amount of transparent conductive oxide (TCO) or is even composed of transparent conductive oxide (TCO). Such an anode A can, for example, contain indium tin oxide, zinc aluminum 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.

[0617] Anode A can (basically) be made of indium tin oxide (ITO) (e.g., (InO3)). 0.9 (SnO2) 0.1The anode A is composed of a hole injection layer (HIL). The roughness of the anode A caused by the transparent conductive oxide (TCO) can be compensated by using a hole injection layer (HIL). Furthermore, the hole injection layer (HIL) can promote the injection of quasi-charge carriers (i.e., holes) by facilitating the transport of quasi-charge carriers from the TCO to the hole transport layer (HTL). The hole injection layer (HIL) can contain poly-(3,4-ethylenedioxythiophene) (PEDOT), polystyrene sulfonate (PSS), MoO2, V2O5, CuPC, or CuI, particularly a mixture of PEDOT and PSS. The hole injection layer (HIL) also prevents metal from diffusing from the anode A into the hole transport layer (HTL). Hole injection layer (HIL) may, for example, contain PEDOT:PSS (poly-(3,4-ethylenedioxythiophene):polystyrene sulfonate), PEDOT (poly-(3,4-ethylenedioxythiophene)), mMTDATA (4,4',4”-tris[phenyl(m-tolyl)amino]triphenylamine), spiro-TAD (2,2',7,7'-tetratetra(N,N-diphenylamino)-9,9'-spirodifluorene), DNTPD (N1,N1'-(biphenyl-4,4'-diyl)bis(N1-phenyl-N4,N4-di-m-tolylphenyl-1,4-diamine). NPB (N,N'-bis(1-naphthyl)-N,N'-bisphenyl-(1,1'-biphenyl)-4,4'-diamine), NPNPB (N,N'-diphenyl-N,N'-bis[4-(N,N-diphenyl-amino)phenyl]benzidine), MeO-TPD (N,N,N',N'-tetra(4-methoxyphenyl)benzidine), HAT-CN (1,4,5,8,9,11-hexaazatriphenyl-hexacarboxynitrile) and / or spiro-NPD (N,N'-diphenyl-N,N'-bis(1-naphthyl)-9,9'-spirodifluorene-2,7-diamine).

[0618] The hole transport layer (HTL) is typically positioned adjacent to the anode A or the hole injection layer (HIL). Any hole transport compound can be used herein. For example, electron-rich heteroaromatic compounds such as triarylamines and / or carbazole can be used as hole transport compounds. The hole transport layer (HTL) can lower the energy barrier between the anode A and the emissive layer EML. The hole transport layer (HTL) can also be an electron blocking layer (EBL). Preferably, the hole transport compound has a relatively high energy level of its triplet state T1. For example, the hole transport layer (HTL) can contain star-shaped heterocycles such as tris(4-carbazole-9-ylphenyl)amine (TCTA), poly-TPD (poly(4-butylphenyl-diphenylamine)), [α]-NPD (N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine), TAPC (4,4'-cyclohexylene-bis[N,N-bis(4-methylphenyl)aniline]), 2-TNATA (4,4',4”-tris[2-naphthyl(phenyl)amino]triphenylamine), spiro-TAD, DNTPD, NPB, NPNPB, M eO-TPD, HAT-CN, and / or Tris-Pcz (9,9'-diphenyl-6-(9-phenyl-9H-carbazol-3-yl)-9H,9'H-3,3'-bicarbazole). Furthermore, the hole transport layer (HTL) may comprise a p-doped layer, which may consist of inorganic or organic dopants in an organic hole transport matrix. Transition metal oxides such as vanadium oxide, molybdenum oxide, or tungsten oxide can be used, for example, as inorganic dopants. Tetrafluorotetracyanoquinone dimethyl ether (F4-TCNQ), cuprous pentafluorobenzoate (Cu(I)pFBz), or transition metal complexes can be used, for example, as organic dopants.

[0619] The electron blocking layer (EBL) may include, for example, mCP (1,3-bis(carbazole-9-yl)benzene), TCTA, 2-TNATA, mCBP (3,3-bis(9H-carbazole-9-yl)biphenyl), Tris-Pcz, CzSi (9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole) and / or DCB (N,N'-dicarbazole-1,4-dimethylbenzene).

[0620] The emissive layer (EML) is typically positioned adjacent to the hole transport layer (HTL). The EML contains at least one organic molecule. Specifically, the EML contains at least one organic molecule E according to the invention. In one embodiment, the EML contains only the organic molecule E according to the invention. Typically, the EML additionally contains one or more host compounds. For example, the host compound is selected from CBP (4,4'-bis(N-carbazolyl)biphenyl), mCP, mCBP, Sif87 ((dibenzo[b,d]thiophene-2-yl)triphenylsilane), CzSi, Sif88 ((dibenzo[b,d]thiophene-2-yl)diphenylsilane), DPEPO (bis[2-(diphenylphosphino)phenyl]ether oxide), 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophene-2-yl)phenyl]-9H-carbazole, etc. [3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole, T2T (2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine), T3T (2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine) and / or TST (2,4,6-tris(9,9'-spirodifluorene-2-yl)-1,3,5-triazine). The host compound should generally be chosen to exhibit a first triplet (T1) and a first singlet (S1) energy level, which are energies higher than the first triplet (T1) and first singlet (S1) energy levels of the organic molecule. Alternatively, the luminescent layer EML additionally comprises one or more host compounds, wherein the host compound is a triplet-triplet annihilation (TTA) material. The TTA material can convert energy from the first excited triplet state T1 to the first excited singlet state S1 via triplet-triplet annihilation. The TTA material should be chosen such that the energy of the lowest excited triplet state T1 of the TTA material is greater than twice the energy of the lowest excited singlet state S1 of the organic molecule according to the invention, i.e., 2T1 (TTA material) > S1 (organic molecule according to the invention).

[0621] In one embodiment of the invention, the luminescent layer EML comprises a so-called hybrid host system having at least one hole-dominant host and one electron-dominant host. In a specific embodiment, the luminescent layer EML comprises only one organic molecule according to the invention and a hybrid host system comprising T2T as an electron-dominant host and selected from CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophene-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole and 9-[3,5-bis(2-dibenzothiophene)phenyl]-9H-carbazole as a hole-dominant host. In other embodiments, the luminescent layer EML comprises 50-80 wt%, preferably 60-75 wt%, of a host selected from CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole and 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole; 10-45 wt%, preferably 15-30 wt%, of T2T; and 5-40 wt%, preferably 10-30 wt%, of an organic molecule according to the invention.

[0622] The electron transport layer (ETL) can be positioned adjacent to the luminescent layer (EML). Any electron transporter can be used herein. Exemplarily, electron-depleted compounds can be used, such as benzimidazole, pyridine, triazole, oxadiazole (e.g., 1,3,4-oxadiazole), phosphine oxide, and sulfone. The electron transporter can also be a star-shaped heterocycle, such as 1,3,5-tris(1-phenyl-1H-benzo[d]imidazole-2-yl)benzene (TPBi). Electron transport layer (ETL) may contain NBphen (2,9-bis(naphthyl-2-yl)-4,7-diphenyl-1,10-phenanthroline), Alq3 (aluminum-tris(8-hydroxyquinoline)), TSPO1 (diphenyl-4-triphenylsilylphenyl-phosphine oxide), BPyTP2 (2,7-bis(2,2'-bipyridin-5-yl)triphenylene), Sif87 ((dibenzo[b,d]thiophene-2-yl)triphenylsilane), Sif88 ((dibenzo[b,d]thiophene-2-yl)diphenylsilane), BmPyPhB (1,3-bis[3,5-bis(pyridin-3-yl)phenyl]benzene) and / or BTB (4,4'-bis-[2-(4,6-diphenyl-1,3,5-triazinyl)]-1,1'-biphenyl). Optionally, the electron transport layer (ETL) can be doped with a material such as Liq. The electron transport layer (ETL) can also block holes, or a hole blocking layer (HBL) can be introduced.

[0623] Hole blocking layers (HBLs) may, for example, contain BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline = Bathocoproline), BAlq (bis(8-hydroxy-2-methylquinoline)-(4-phenylphenoxy)aluminum), NBphen (2,9-bis(naphthyl-2-yl)-4,7-diphenyl-1,10-phenanthroline), Alq3 (aluminum-tris(8-hydroxyquinoline)), TSPO1 (diphenyl- 4-Triphenylsilylphenylphosphine oxide), T2T (2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine), T3T (2,4,6-tris(tribiphenyl-3-yl)-1,3,5-triazine), TST (2,4,6-tris(9,9'-spirodifluorene-2-yl)-1,3,5-triazine) and / or TCB / TCP (1,3,5-tris(N-carbazolyl)benzene / 1,3,5-tris(carbazolyl-9-yl)benzene).

[0624] The cathode C can be positioned adjacent to the electron transport layer (ETL). The cathode C can, for example, comprise a metal (e.g., Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, Li, Ca, Ba, Mg, In, W, or Pd) or a metal alloy, or be composed 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 C can also be (substantially) composed of opaque metals such as Mg, Ca, or Al. Alternatively or additionally, the cathode C can also comprise graphite and / or carbon nanotubes (CNTs). Alternatively, the cathode C can also be composed of nanoscale silver wires.

[0625] The OLED may optionally include a protective layer (which may be referred to as the electron injection layer (EIL)) between the electron transport layer (ETL) and the cathode C. This layer may contain lithium fluoride, cesium fluoride, silver, Liq (lithium 8-hydroxyquinoline), Li2O, BaF2, MgO and / or NaF.

[0626] Optionally, the electron transport layer (ETL) and / or hole blocking layer (HBL) may also contain one or more host compounds H.

[0627] To further modify the emission and / or absorption spectra of the emissive layer EML, the emissive layer EML may further include one or more other emitter molecules F. Such emitter molecules F can be any emitter molecules known in the art. Preferably, such emitter molecules F are molecules whose structure differs from that of the organic molecule E according to the invention. Emitter molecules F may optionally be TADF emitters. Alternatively, emitter molecules F may optionally be fluorescent and / or phosphorescent emitter molecules capable of altering the emission and / or absorption spectra of the emissive layer EML. Exemplarily, triplet and / or singlet excitons may transfer from the organic molecule according to the invention to emitter molecules F before relaxing to the ground state S0 by emitting light that is typically redshifted compared to light emitted by the organic molecule. Optionally, emitter molecules F may also induce a two-photon effect (i.e., absorption of two photons at half the maximum energy of absorption).

[0628] Optionally, the optoelectronic device (e.g., OLED) can be, for example, a substantially white optoelectronic device. For example, such a white optoelectronic device may comprise at least one (deep) blue emitter molecule and one or more emitter molecules that emit green and / or red light. Then, energy transmittance may optionally exist between the two or more types of molecules as described above.

[0629] As used herein, unless otherwise defined in a specific context, the names of the colors of the emitted and / or absorbed light are as follows:

[0630] Purple: Wavelength range >380-420nm;

[0631] Deep blue: wavelength range >420-480nm;

[0632] Sky blue: wavelength range >480-500nm;

[0633] Green: Wavelength range >500-560nm;

[0634] Yellow: Wavelength range >560-580nm;

[0635] Orange: Wavelength range >580-620nm;

[0636] Red: Wavelength range >620-800nm.

[0637] Regarding emitter molecules, this color refers to the emission maximum. Thus, for example, a dark blue emitter has an emission maximum in the range of >420nm to 480nm, a sky blue emitter has an emission maximum in the range of >480nm to 500nm, a green emitter has an emission maximum in the range of >500nm to 560nm, and a red emitter has an emission maximum in the range of >620nm to 800nm.

[0638] The deep blue emitter preferably has a maximum emission value below 480 nm, more preferably below 470 nm, even more preferably below 465 nm or even below 460 nm. It is typically above 420 nm, preferably above 430 nm, more preferably above 440 nm or even above 450 nm.

[0639] Therefore, other aspects of the present invention relate to OLEDs with a density of 1000 cd / m². 2 It exhibits an external quantum efficiency greater than 8%, more preferably greater than 10%, more preferably greater than 13%, even more preferably greater than 15% or even greater than 20%, and / or exhibits a maximum emission value at 420 nm to 500 nm, preferably at 430 nm to 490 nm, more preferably at 440 nm to 480 nm, even more preferably at 450 nm to 470 nm, and / or at 500 cd / m 2 The LT80 value exhibits a value greater than 100h, preferably greater than 200h, more preferably greater than 400h, even more preferably greater than 750h, or even greater than 1000h. Therefore, other aspects of the present invention relate to OLEDs whose emission exhibits CIEy color coordinates of less than 0.45, preferably less than 0.30, more preferably less than 0.20, or even more preferably less than 0.15, or even less than 0.10.

[0640] Other aspects of the invention relate to OLEDs that emit light at different color points. According to the invention, the OLED emits light having a narrow emission band (small full width at half maximum (FWHM)). In one aspect, the OLED according to the invention emits light with an FWHM of a main emission peak of less than 0.30 eV, preferably less than 0.25 eV, more preferably less than 0.18 eV, even more preferably less than 0.15 eV, or even less than 0.12 eV.

[0641] Other aspects of the invention relate to OLEDs that emit light at different color points. According to the invention, the OLED emits light having a narrow emission band (small full width at half maximum (FWHM)). In one aspect, the OLED according to the invention emits light with an FWHM of a main emission peak of less than 0.30 eV, preferably less than 0.25 eV, more preferably less than 0.18 eV, even more preferably less than 0.15 eV or even less than 0.12 eV, and its excited-state lifetime is not greater than 10 μs, not greater than 8 μs, particularly not greater than 6 μs, more preferably not greater than 5 μs or not greater than 4 μs, even more preferably not greater than 3 μs.

[0642] Other aspects of the invention relate to OLEDs that emit light having CIEx and CIEy color coordinates close to the primary color blue (CIEx = 0.131 and CIEy = 0.046) as defined by ITU-R Recommendation BT.2020 (Rec.2020), and are therefore suitable for use in ultra-high definition (UHD) displays (e.g., UHD-TV). Therefore, other aspects of the present invention relate to OLEDs whose emission exhibits CIEx color coordinates of 0.02 to 0.30, preferably 0.03 to 0.25, more preferably 0.05 to 0.20, or even more preferably 0.08 to 0.18, or even more preferably 0.10 to 0.15 and / or CIEy color coordinates of 0.00 to 0.45, preferably 0.01 to 0.30, more preferably 0.02 to 0.20, or even more preferably 0.03 to 0.15, or even more preferably 0.04 to 0.10.

[0643] In other respects, the present invention relates to a method for generating optoelectronic devices. In this case, the organic molecules of the present invention are used.

[0644] Optoelectronic devices, particularly OLEDs according to the present invention, can be manufactured by any method of vapor deposition and / or liquid processing. Therefore, at least one layer is...

[0645] -Prepared by sublimation method

[0646] -Prepared by organic vapor deposition method.

[0647] -Prepared by carrier gas sublimation method.

[0648] - Solution treatment or printing.

[0649] Methods for manufacturing optoelectronic devices, particularly OLEDs according to the present invention, are known in the art. Different layers are deposited individually and sequentially on a suitable substrate by subsequent deposition methods. The individual layers can be deposited using the same or different deposition methods.

[0650] For example, vapor deposition methods 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 can be processed by solutions or dispersions using suitable solvents. Solution deposition methods include, for example, spin coating, dip coating, and jet printing. Liquid processing can optionally be performed in an inert atmosphere (e.g., in a nitrogen atmosphere), and the solvent can be completely or partially removed by methods known in the art.

[0651] Example

[0652] General Synthesis Scheme I

[0653] General Synthesis Scheme I provides a synthetic scheme for the organic molecule according to the present invention, wherein R I =R X R II =R IX R III =R VIII R IV =R VII R V =R VI :

[0654] General procedure for synthesizing AAV0:

[0655]

[0656]

[0657] General procedure for synthesizing AAV0:

[0658]

[0659] E0 (1.00 equivalent), 1,3-dichloro-5-iodobenzene (1.10 equivalent; CAS: 3032-81-3), tris(dibenzylacetone)dipalladium (Pd2(dba)3; 0.01 equivalent; CAS: 51364-51-3), tri-tert-butylphosphine (P( t Bu)3, CAS: 13716-12-6, 0.04 equivalent) and sodium tert-butoxide (NaO) t Bu (2.00 equivalents) was stirred in toluene at 60 °C for 25 min under a nitrogen atmosphere. After cooling to room temperature (rt), the reaction mixture was extracted with ethyl acetate and brine, and the phases were separated. The combined organic layers were dried over MgSO4 and then the solvent was removed under reduced pressure. The crude product was purified by recrystallization or column chromatography to give E1a as a solid.

[0660] General procedure for synthesizing AAV1:

[0661]

[0662] E1a (1.00 equivalent), E1b (5.00 equivalent), tris(dibenzylacetone)dipalladium (Pd2(dba)3; 0.02 equivalent; CAS: 51364-51-3), tri-tert-butylphosphine (P( t Bu)3, CAS: 13716-12-6, 0.08 equivalent) and sodium tert-butoxide (NaO) t Bu (5.00 equivalents) was stirred in toluene at 110 °C for 260 h under a nitrogen atmosphere. After cooling to room temperature (rt), the reaction mixture was extracted with toluene and brine, and the phases were separated. The combined organic layers were dried over MgSO4 and then the solvent was removed under reduced pressure. The crude product was purified by recrystallization or column chromatography to give I1 as a solid.

[0663] General procedure for synthesizing AAV2:

[0664]

[0665] I1 (1.20 equivalent), E2 (1.00 equivalent), tris(dibenzylacetone)dipalladium (Pd2(dba)3; 0.02 equivalent; CAS: 51364-51-3), tri-tert-butylphosphine (P( t Bu)3, CAS: 13716-12-6, 0.08 equivalent) and sodium tert-butoxide (NaO) t Bu (5.00 equivalents) was stirred in toluene at 120 °C for 2 hours under a nitrogen atmosphere. After cooling to room temperature (rt), the reaction mixture was extracted with toluene and brine, and the phases were separated. The combined organic layers were dried over MgSO4 and then the solvent was removed under reduced pressure. The crude product was purified by recrystallization or column chromatography to give I2 as a solid.

[0666] General procedure for synthesizing AAV3:

[0667]

[0668] I2 (1.00 equivalent), 1,3-diiodobenzene (2.80 equivalent; CAS: 626-00-6), tris(dibenzylacetone)dipalladium (Pd2(dba)3; 0.02 equivalent; CAS: 51364-51-3), tri-tert-butylphosphine (P( t Bu)3, CAS: 13716-12-6, 0.09 equivalent) and sodium tert-butoxide (NaO) tBu (11.40 equivalents) was stirred overnight in toluene at 110 °C under a nitrogen atmosphere. After cooling to room temperature (rt), the reaction mixture was extracted with toluene and brine, and the phases were separated. The combined organic layers were dried over MgSO4 and then the solvent was removed under reduced pressure. The crude product was purified by recrystallization or column chromatography to give I3 as a solid.

[0669] General procedure for synthesizing AAV4:

[0670]

[0671] Boron tribromide (CAS 10294-33-4, 4.00 equivalents) was slowly added to a solution of o-dichlorobenzene (I3, 1.00 equivalents) under a nitrogen atmosphere. The reaction mixture was stirred overnight at 180°C and quenched by adding N,N-diisopropylethylamine (CAS 7087-68-5; 16.0 equivalents) after cooling to room temperature. The reaction mixture was extracted with dichloromethane and water, and the phases were separated. The combined organic layers were dried over MgSO4 and then the solvent was removed under reduced pressure. The crude product was purified by recrystallization or column chromatography to give P1 as a solid.

[0672] General Synthesis Scheme II

[0673]

[0674]

[0675] General procedure for synthesizing AAV5:

[0676]

[0677] E1a (1.20 equivalent), E5 (1.00 equivalent), tris(dibenzylacetone)dipalladium (Pd2(dba)3; 0.02 equivalent; CAS: 51364-51-3), tri-tert-butylphosphine (P( t Bu)3, CAS: 13716-12-6, 0.08 equivalent) and sodium tert-butoxide (NaO) t Bu (2.00 equivalents) was stirred in toluene at 110 °C for 11 hours under a nitrogen atmosphere. After cooling to room temperature (rt), the reaction mixture was extracted with toluene and brine, and the phases were separated. The combined organic layers were dried over MgSO4 and then the solvent was removed under reduced pressure. The crude product was purified by recrystallization or column chromatography to give I5 as a solid.

[0678] General procedure for synthesizing AAV6:

[0679]

[0680] E6 (1.00 equivalent), I5 (2.20 equivalent), tris(dibenzylacetone)dipalladium (Pd2(dba)3; 0.02 equivalent; CAS: 51364-51-3), tri-tert-butylphosphine (P( t Bu)3, CAS: 13716-12-6, 0.08 equivalent) and sodium tert-butoxide (NaO) t Bu (4.00 equivalents) was stirred overnight in toluene at 110 °C under a nitrogen atmosphere. After cooling to room temperature (rt), the reaction mixture was extracted with toluene and brine, and the phases were separated. The combined organic layers were dried over MgSO4 and then the solvent was removed under reduced pressure. The crude product was purified by recrystallization or column chromatography to give I6 as a solid.

[0681] General procedure for synthesizing AAV7:

[0682]

[0683] Boron tribromide (CAS 10294-33-4, 4.00 equivalents) was slowly added to a solution of o-dichlorobenzene (I6, 1.00 equivalents) under a nitrogen atmosphere. The reaction mixture was stirred overnight at 180 °C and quenched by adding N,N-diisopropylethylamine (CAS 7087-68-5; 16.0 equivalents) after cooling to room temperature. The reaction mixture was extracted with dichloromethane and water, and the phases were separated. The combined organic layers were dried over MgSO4 and then the solvent was removed under reduced pressure. The crude product was purified by recrystallization or column chromatography to give P2 as a solid.

[0684] General Synthesis Scheme III

[0685]

[0686]

[0687] General procedure for synthesizing AAV8:

[0688]

[0689] 3-Bromochlorobenzene (1.50 equivalent; CAS 108-37-2), E8 (1.00 equivalent), tris(dibenzylacetone)dipalladium (Pd2(dba)3; 0.02 equivalent; CAS: 51364-51-3), tri-tert-butylphosphine (P( t Bu)3; 0.08 equivalent; CAS: 13716-12-6) and sodium tert-butoxide (NaO) tBu (4.00 equivalents) was stirred in toluene at 80 °C for 12 hours under a nitrogen atmosphere. After cooling to room temperature (rt), the reaction mixture was extracted with toluene and brine, and the phases were separated. The combined organic layers were dried over MgSO4, and then the solvent was removed under reduced pressure. The crude product was purified by recrystallization or column chromatography to give I8 as a solid.

[0690] General procedure for synthesizing AAV9:

[0691]

[0692] The following ingredients were added: I8 (1.00 equivalent), E1b (1.50 equivalent), tris(dibenzylacetone)dipalladium (Pd2(dba)3; 0.06 equivalent; CAS: 51364-51-3), and tri-tert-butylphosphine (P( t Bu)3; 0.02 equivalent; CAS: 13716-12-6) and sodium tert-butoxide (NaO) t Bu (6.00 equivalents) was stirred in toluene at 110 °C for 72 hours under a nitrogen atmosphere. After cooling to room temperature (rt), the reaction mixture was extracted with toluene and brine, and the phases were separated. The combined organic layers were dried over MgSO4 and then the solvent was removed under reduced pressure. The crude product was purified by recrystallization or column chromatography to give I9 ​​as a solid.

[0693] General procedure for synthesizing AAV8a:

[0694]

[0695] E1a (1.20 equivalent), E1b (1.00 equivalent), tris(dibenzylacetone)dipalladium (Pd2(dba)3; 0.02 equivalent; CAS: 51364-51-3), tri-tert-butylphosphine (P( t Bu)3, CAS: 13716-12-6, 0.08 equivalent) and sodium tert-butoxide (NaO) t Bu (2.00 equivalents) was stirred in toluene at 100 °C for 69 hours under a nitrogen atmosphere. After cooling to room temperature (rt), the reaction mixture was extracted with toluene and brine, and the phases were separated. The combined organic layers were dried over MgSO4 and then the solvent was removed under reduced pressure. The crude product was purified by recrystallization or column chromatography to give I8a as a solid.

[0696] General procedure for synthesizing AAV9a:

[0697]

[0698] The following ingredients were added: I8a (0.66 equivalent), 1,3-diiodobenzene (1.00 equivalent; CAS: 626-00-6), tris(dibenzylacetone)dipalladium (Pd2(dba)3; 0.01 equivalent; CAS: 51364-51-3), and tri-tert-butylphosphine (P( t Bu)3, CAS: 13716-12-6, 0.04 equivalent) and sodium tert-butoxide (NaO) t Bu (4.00 equivalents) was stirred in toluene at 70°C for 3 hours under a nitrogen atmosphere. After cooling to room temperature (rt), the reaction mixture was extracted with ethyl acetate and brine, and the phases were separated. The combined organic layers were dried over MgSO4 and then the solvent was removed under reduced pressure. The crude product was purified by recrystallization or column chromatography to give I9a as a solid.

[0699] General procedure for synthesizing AAV10:

[0700]

[0701] I9a (1.00 equivalent), I9 (2.55 equivalent), tris(dibenzylacetone)dipalladium (Pd2(dba)3; 0.04 equivalent; CAS: 51364-51-3), tri-tert-butylphosphine (P( t Bu)3, CAS: 13716-12-6, 0.16 equivalent) and sodium tert-butoxide (NaO) t Bu (3.50 equivalents) was stirred overnight in toluene at 110 °C under a nitrogen atmosphere. After cooling to room temperature (rt), the reaction mixture was extracted with toluene and brine, and the phases were separated. The combined organic layers were dried over MgSO4 and then the solvent was removed under reduced pressure. The crude product was purified by recrystallization or column chromatography to give I6 as a solid.

[0702] General procedure for synthesizing AAV7:

[0703]

[0704] Boron tribromide (CAS 10294-33-4, 4.00 equivalents) was slowly added to a solution of o-dichlorobenzene (I6, 1.00 equivalents) under a nitrogen atmosphere. The reaction mixture was stirred overnight at 180 °C and quenched by adding N,N-diisopropylethylamine (CAS 7087-68-5; 16.0 equivalents) after cooling to room temperature. The reaction mixture was extracted with dichloromethane and water, and the phases were separated. The combined organic layers were dried over MgSO4 and then the solvent was removed under reduced pressure. The crude product was purified by recrystallization or column chromatography to give P2 as a solid.

[0705] Cyclic voltammetry

[0706] From dichloromethane or a suitable solvent and a suitable supporting electrolyte (e.g., 0.1 mol / L tetrabutylammonium hexafluorophosphate) having 10 -3 Cyclic voltammetry was performed on solutions of organic molecules at a concentration of mol / L. Measurements were performed at room temperature under a nitrogen atmosphere using a three-electrode assembly (working and counter electrodes: Pt line, reference electrode: Pt line) and using FeCp2 / FeCp2 + Calibration was performed using ferrocene as an internal standard. HOMO data were corrected relative to a saturated calomel electrode (SCE) using ferrocene as an internal standard.

[0707] Density functional theory calculations

[0708] The molecular structure was optimized using the BP86 functional and the identity analytical method (RI). Excitation energies were calculated using the structure optimized with the time-correlated DFT (TD-DFT) method (BP86). Orbital and excited-state energies were calculated using the B3LYP functional. The Def2-SVP basis set and an m4 grid were used for numerical integration. The Turbomole package was used for all calculations.

[0709] Optical physical measurement

[0710] Sample pretreatment: spin coating

[0711] Equipment: Spin150, SPS euro.

[0712] The sample concentration was 0.2 mg / ml, dissolved in a suitable solvent of toluene / DCM.

[0713] Program: 7; 30 seconds, at 2000 U / min. After coating, dry the film at 70°C for 1 minute.

[0714] Photoluminescence spectroscopy and time-correlated single-photon counting (TCSPC)

[0715] Steady-state emission spectra were recorded using a Horiba Scientific Modell FluoroMax-4 equipped with a 150W xenon arc lamp, excitation and emission monochromators, a Hamamatsu R928 photomultiplier tube, and a time-correlated single-photon counting option. Standard calibration fits were used to correct the emission and excitation spectra.

[0716] The excited-state lifetime was determined using the same system with a TCSPC method featuring an FM-2013 device and a Horiba Yvon TCSPC hub.

[0717] Excitation source:

[0718] NanoLED 370 (wavelength: 371nm, pulse duration: 1.1ns)

[0719] NanoLED 290 (wavelength: 294nm, pulse duration: <1ns)

[0720] SpectraLED 310 (wavelength: 314nm)

[0721] SpectraLED 355 (wavelength: 355nm).

[0722] Data analysis (exponential fit) was performed using the DataStation and DAS6 software suites. A chi-square test was used to specify the fit.

[0723] Time-resolved PL spectra in the μs and ns ranges (FS5)

[0724] Time-resolved photon emission (PL) measurements were performed on an FS5 fluorescence spectrometer from Edinburgh Instruments. The better focusing allowed for an optimized signal-to-noise ratio compared to measurements on a HORIBA device, which is advantageous for the FS5 system, especially for transient PL measurements of delayed fluorescence characteristics. The continuous light source was a 150W xenon arc lamp, and the selected wavelength was chosen by a Czerny-Turner monochromator, which was also used to set the specific emission wavelength. Sample emission was directed to a sensitive R928P photomultiplier tube (PMT), allowing detection of single photons with peak quantum efficiencies up to 25% in the spectral range of 200 nm to 870 nm. The detector was a temperature-stable PMT providing dark counts (counts per second) below 300 cps. Finally, to determine the transient decay lifetime of the delayed fluorescence, a tail fit using three exponential functions was applied. This was achieved by using the corresponding amplitude A... i For a specific lifetime τ i Weighting,

[0725]

[0726] Determining the delayed fluorescence lifetime τ DF .

[0727] Photoluminescence quantum yield measurement

[0728] For photoluminescent quantum yield (PLQY) measurements, the absolute PL quantum yield measurement system C9920-03G (Hamamatsu Photonics) was used. Quantum yield and CIE coordinates were determined using software U6039-05 version 3.6.0.

[0729] The maximum emission value is given in nm, the quantum yield Φ is given in % and the CIE coordinates are given in x and y values.

[0730] PLQY is determined using the following method:

[0731] 1) Quality Assurance: Anthracene (known concentration) in ethanol is used as a reference.

[0732] 2) Excitation wavelength: Determine the maximum absorption value of organic molecules and use this wavelength to excite the molecules.

[0733] 3) Measurement

[0734] The quantum yield of a membrane sample (2 wt% emitter in PMMA) was measured under a nitrogen atmosphere. The yield was calculated using the following equation:

[0735]

[0736] Where n 光子 Indicates the photon count and Int. indicates intensity.

[0737] Production and characterization of optoelectronic devices

[0738] Optoelectronic devices, such as OLED devices, containing organic molecules according to the invention can be produced via a vacuum evaporation method. If the layer contains more than one compound, the weight percentage of the one or more compounds is given as %. The total weight percentage value is equal to 100%, so if no value is given, the fraction of the compound is equal to the difference between the given value and 100%.

[0739] (Incompletely optimized) OLEDs are characterized using standard methods and measurements of electroluminescence spectrum, intensity-dependent external quantum efficiency (in percentage) (calculated using light detected by a photodiode), and current. The OLED device lifetime is extracted from the change in brightness during operation at a constant current density. The LT50 value corresponds to the time point where the measured brightness decreases to 50% of the initial brightness; similarly, the LT80 value corresponds to the time point where the measured brightness decreases to 80% of the initial brightness, the LT95 value corresponds to the time point where the measured brightness decreases to 95% of the initial brightness, and so on.

[0740] Perform accelerated lifetime measurements (e.g., apply increased current density). At 500 cd / m 2 The following exemplary LT80 value is determined using the following equation:

[0741]

[0742] Where L0 represents the initial brightness at the applied current density.

[0743] These values ​​correspond to the average of several pixels (usually 2 to 8), and give the standard deviation between these pixels.

[0744] HPLC-MS

[0745] HPLC-MS analysis was performed on an Agilent HPLC (1260 series) equipped with an MS detector (ThermoLTQ XL).

[0746] For example, a typical HPLC method is as follows: An Agilent reversed-phase column (3.0 mm × 100 mm, 2.7 μm particle size, Poroshell 120EC-C18, 3.0 x 100 mm, 2.7 μm HPLC column) is used in the HPLC. HPLC-MS measurements are performed at room temperature (rt) according to the following gradient.

[0747]

[0748] Use the following solvent mixture containing 0.1% formic acid:

[0749] Solvent A: <![CDATA[H2O(10%)]]> MeCN (90%) Solvent B: <![CDATA[H2O(90%)]]> MeCN (10%) Solvent C: THF (50%) MeCN (50%)

[0750] Take a 2 μL injection volume from a solution of the analyte with a concentration of 0.5 mg / mL for measurement.

[0751] The probe is ionized using an atmospheric pressure chemical ionization (APCI) source or an atmospheric pressure photoionization (APPI) source in positive (APCI+) or negative (APCI-) ionization mode.

[0752] Example 1

[0753]

[0754] According to the following synthesis example 1

[0755] AAV1 (73% yield), wherein 3,5-dichloro-N,N-diphenylaniline [1329428-05-8] is used as compound E1a and 2-fluoroaniline [348-54-9] is used as compound E1b;

[0756] AAV2 (59% yield), in which 3-bromotriphenylamine [78600-33-6] is used as compound E2;

[0757] AAV3 (94% yield);

[0758] AAV4 (25% yield).

[0759] MS (HPLC-MS): m / z (retention time) = 1503.3 (7.13 min).

[0760] Example 1 (2 wt% in PMMA) showed a maximum emission at 460 nm, a full width at half maximum (FWHM) of 0.10 eV (17 nm), CIEx and CIEy coordinates of 0.14 and 0.07, respectively, a PLQY of 71%, and an excited-state lifetime of 2.9 μs.

[0761] Example 2

[0762]

[0763] According to the following synthesis example 2

[0764] AAV5 (54% yield), wherein 3,5-dichloro-N,N-diphenylaniline [1329428-05-8] is used as compound E1a and N,N,N'-triphenyl-phenyl-1,3-diamine [1554227-26-7] is used as compound E5;

[0765] AAV6 (21% yield), wherein N,N'-diphenyl-m-phenylenediamine [5905-36-2] is used as compound E6;

[0766] AAV7 (17% yield).

[0767] MS (HPLC-MS): m / z (retention time) = 1431.4 (7.99 min).

[0768] Example 2 (2 wt% in PMMA) has a maximum emission at 471 nm, a full width at half maximum (FWHM) of 0.11 eV (20 nm), CIEx and CIEy coordinates of 0.13 and 0.15, respectively, and PLQY of 51%.

[0769] Example 3

[0770]

[0771] According to the following synthesis example 3

[0772] AAV8 (99% yield), in which bis(4-biphenyl)amine [102113-98-4] is used as compound E8;

[0773] AAV9 (40% yield), in which 3-bromotriphenylamine [78600-33-6] is used as compound E1b;

[0774] AAV8a (55% yield), wherein 3,5-dichloro-N,N-diphenylaniline [1329428-05-8] and aniline [62-53-3] are used as compounds E1a and E1b, respectively;

[0775] AAV9a (73% yield);

[0776] AAV10 (14% yield);

[0777] AAV7 (17% yield).

[0778] MS (HPLC-MS): m / z (retention time) = 1735.8 (8.56 min).

[0779] Example 3 (2 wt% in PMMA) has a maximum emission at 473 nm, a full width at half maximum (FWHM) of 0.10 eV (19 nm), and CIEx and CIEy coordinates of 0.12 and 0.15, respectively.

[0780] Example 4

[0781]

[0782] According to the following synthesis example 4

[0783] AAV0 (94% yield), in which bis(4-biphenyl)amine [102113-98-4] is used as compound E0;

[0784] AAV1 (87% yield), in which aniline [62-53-3] is used as compound E1b;

[0785] AAV2 (54% yield), in which 3-bromotriphenylamine [78600-33-6] is used as compound E2;

[0786] AAV3 (54% yield);

[0787] AAV4 (21% yield).

[0788] MS (HPLC-MS): m / z (retention time) = 1735.8 (8.62 min).

[0789] Example 4 (2 wt% in PMMA) has a maximum emission at 472 nm, a full width at half maximum (FWHM) of 0.11 eV (20 nm), and CIEx and CIEy coordinates of 0.13 and 0.16, respectively.

[0790] Example 5

[0791]

[0792] According to the following synthesis example 5

[0793] AAV1 (58% yield), wherein 3,5-dichloro-N,N-diphenylaniline [1329428-05-8] is used as compound E1a and 2,6-dimethylaniline [87-62-7] is used as compound E1b;

[0794] AAV2 (39% yield), in which 3-bromotriphenylamine [78600-33-6] is used as compound E2;

[0795] AAV3 (55% yield);

[0796] AAV4 (3% yield).

[0797] MS (HPLC-MS): m / z (retention time) = 1543.6 (8.39 min).

[0798] Example 5 (2 wt% in PMMA) has a maximum emission at 469 nm, a full width at half maximum (FWHM) of 0.10 eV (18 nm), CIEx and CIEy coordinates of 0.13 and 0.16, respectively, and PLQY of 75%.

[0799] Other examples of organic molecules of the present invention

[0800]

[0801]

[0802]

[0803]

[0804]

[0805]

[0806]

[0807]

[0808]

[0809]

[0810]

[0811]

[0812]

[0813]

[0814]

[0815]

[0816]

Claims

1. Organic molecule, including the structure of formula III: Formula III in R a Each time it appears, independently select from the following groups: Hydrogen, deuterium, CF3, CN, F, Cl, Br, I C1-C 40 -alkyl, The C1-C 40 -The alkyl group is optionally replaced by one or more substituents R 5 replace; C1-C 40 -alkoxy, The C1-C 40 -Alkoxy group is optionally replaced by one or more substituents R 5 replace; C1-C 40 -Thioalkoxy, The C1-C 40 -Thioalkoxy group is optionally replaced by one or more substituents R 5 Replace; and Ph, The Ph is optionally replaced by one or more substituents R. 5 replace; R 5 Each time it appears, independently select from the following groups: Hydrogen, deuterium, F, Cl, Br, I, Cl-C 12 -alkyl and Ph; R I R II R III R IV R V R VI R VII R VIII R IX and R X Each time it appears, independently select from the following groups: Hydrogen, deuterium, CF3, CN, F, Cl, Br, I C1-C 40 -alkyl, The C1-C 40 -The alkyl group is optionally replaced by one or more substituents R 4 replace; C1-C 40 -alkoxy, The C1-C 40 -Alkoxy group is optionally replaced by one or more substituents R 4 replace; C1-C 40 -Thioalkoxy, The C1-C 40 -Thioalkoxy group is optionally replaced by one or more substituents R 4 Replace; and Ph, The Ph is optionally replaced by one or more substituents R. 4 replace; R 4 Each time it appears, independently select from the following groups: Hydrogen, deuterium, F, Cl, Br, I, CF3, CN C1-C5-alkyl, In this embodiment, one or more hydrogen atoms may be independently substituted by deuterium, F, Cl, Br, I, CN or CF3; C1-C5-alkoxy, In this embodiment, one or more hydrogen atoms may be independently substituted by deuterium, F, Cl, Br, I, CN, or CF3; and C1-C5-thioalkoxy, In this configuration, one or more hydrogen atoms may be independently substituted by deuterium, F, Cl, Br, I, CN, or CF3.

2. The organic molecule according to claim 1, wherein R I R II R III R IV R V R VI R VII R VIII R IX and R X Each time it appears, independently select from the following groups: hydrogen, Me、 i Pr、 t Bu、CN、CF3、F, Ph, wherein Ph is optionally selected independently of one or more Me, i Pr, t Substituent substitutions in the group consisting of Bu, CN, CF3 and F.

3. The organic molecule according to claim 1, wherein R a Each time it appears, independently select from the following groups: hydrogen, Me、 i Pr、 t Bu、CN、CF3、F, Ph, wherein Ph is optionally selected independently of one or more Me, i Pr, t Substituent substitutions in the group consisting of Bu and F.

4. The organic molecule according to claim 1, wherein R V = R X And R I = R VI .

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

6. The use according to claim 5, wherein the optoelectronic device is selected from the group consisting of: Luminescent electrochemical cells, organic diodes, organic solar cells, organic transistors, organic lasers, and downconversion elements.

7. The use according to claim 6, wherein the optoelectronic device is selected from the group consisting of: Organic light-emitting diodes and organic field-effect transistors.

8. The use according to claim 6, wherein the optoelectronic device is selected from the group consisting of: Organic light-emitting diode (OLED) sensor.

9. A composition comprising: (a) An organic molecule according to any one of claims 1 to 4, in the form of an emitter and / or a host, and (b) Emitters and / or host materials different from those of the organic molecules, and (c) Optional dyes and / or solvents.

10. Optoelectronic devices, including: - Substrate, - Anode, and - A cathode, wherein the anode or the cathode is disposed on the substrate, and - A light-emitting layer disposed between the anode and the cathode and comprising an organic molecule according to any one of claims 1 to 4 or a composition according to claim 9.

11. The optoelectronic device according to claim 10, wherein it is in the form of a device selected from the group consisting of a light-emitting electrochemical cell, an organic diode, an organic solar cell, an organic transistor, an organic laser, and a down-conversion element.

12. The optoelectronic device according to claim 11, wherein it is in the form of a device selected from the group consisting of organic light-emitting diodes and organic field-effect transistors.

13. The optoelectronic device according to claim 11, wherein it is in the form of a device selected from the group consisting of organic light-emitting diode sensors.

14. A method for producing an optoelectronic device, wherein an organic molecule according to any one of claims 1 to 4 or a composition according to claim 9 is used, comprising processing the organic molecule by a vacuum evaporation method or by treating it from a solution.

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