Compounds containing phthalimide and carbazole or its analogues for organic optoelectronic devices

Abstract

This invention relates to a purely organic molecule of formula A1 and its use in optoelectronic devices. (A1)

Description

[0001] This application is a divisional application of the invention patent application filed on August 1, 2017, with application number 201780048607.9 and entitled "Compounds containing phthalimide and carbazole or similar substances for organic optoelectronic devices". Technical Field

[0002] This invention relates to pure organic molecules and their use in organic light-emitting diodes (OLEDs) and other organic optoelectronic devices. Background Technology

[0003] Organic optoelectronic devices are characterized by the conversion of electrical energy into photons (organic light-emitting diodes, OLEDs, or light-emitting electrochemical cells, LEECs) or the reverse process (organic photovoltaic devices, OPVs). It is crucial to perform these processes with maximum efficiency. Therefore, in the field of LEDs, it is ideal to use materials with the highest photoluminescence quantum yield. The limited efficiency of OLED materials can be improved by using highly efficient materials exhibiting thermally activated delayed fluorescence (TADF), as it can utilize up to 100% of the excitons formed in OLEDs, instead of the 25% required for pure fluorescent materials. It is also possible to convert the generated triplet excitons into singlet excitons, from which photons can be emitted. This thermal repopulation requires a small band gap between the lowest excited singlet level (S1) and the triplet level (T1). This can be achieved, for example, by using copper(I) complexes (see, in this respect, for example, H. Yersin, U. Monkowius, T. Fischer, T. Hofbeck, WO 2010 / 149748 A1), or by using purely organic materials (see, in this respect, for example, Q. Zhang et al., J. Am. Chem. Soc. 2012, 134, 14706, WO 2013161437A1).

[0004] Intensive research in this field indicates a continued significant demand for novel materials. For example, there is still a need for deep blue and sky blue TADF OLEDs. Current blue TADF materials often exhibit long exciton lifetimes and / or low photoluminescence quantum yields, which are detrimental to efficient and long-lived OLEDs. Measurements suitable for effective blue OLEDs include power efficiency in cd / A and the y-value of the CIE color coordinates of the emitted light (CIE). y The quotient of ), that is, normalized to CIE yEfficiency of value. Similar to the properties of the materials already mentioned, availability is also relevant to commercialization. This includes the availability of synthetic units, as well as the complexity of actually synthesizing functional materials, including their purification. Detailed Implementation

[0005] The problem solved by this invention is to provide molecules suitable for use as emitter materials in blue light-emitting OLEDs.

[0006] Surprisingly, it has been found that by using a suitable combination of donor and phthalimide acceptor units, molecules with emission maxima below 491 nm, exhibiting high quantum yield and short exciton lifetimes, can be obtained. Since the efficiency of a component after optimized stacking design is typically directly related to the photoluminescence quantum yield (PLQY) of the emitter material, a technical index similar to the efficiency index of known blue OLEDs was determined for the molecule according to the present invention. This Blue Material Index (BMI) is calculated as PLQY (in %) and the CIE of the light emitted by the molecule according to the present invention. y The quotient of color coordinates.

[0007] The organic molecules according to the present invention comprise or are composed of the structure of formula A1.

[0008]

[0009] in

[0010] A is the same or different in all cases and is CR. b Or N;

[0011] R N The group consists of the following: methyl, phenyl, methylbenzyl, mesitylene, naphthyl, biphenyl, naphthylphenyl, biphenyl and 2,4,6-triphenylphenyl.

[0012] R a In each case, the group consisting of H, deuterium, alkyl, and aryl is chosen independently.

[0013] R b In each case, it is the same or different and is H, deuterium, CF3, C(=O)R 1 CN, unsubstituted or with one or more R 2 Substituted alkyl or aryl groups, which are unsubstituted or have undergone one or more R... 2 Substituted and optionally further substituted with one or more unsubstituted alkyl groups and / or with one or more unsubstituted or alkyl-substituted aryl groups, heteroaryl groups, which are unsubstituted or substituted with one or more R groups. 2and / or substituted with one or more unsubstituted alkyl groups and / or substituted with one or more unsubstituted or alkyl-substituted aryl groups, groups of formula T1 or group of formula T2:

[0014]

[0015] It has the following definition:

[0016] R N2 It is an alkyl group, unsubstituted or derived from one or more R groups. N3 Substituted aryl groups, or unsubstituted or via one or more R groups N3 Replacement of heteroaryl compounds.

[0017] R N3 It is alkyl, aryl, or heteroaryl.

[0018] R 1 In each case, it is either unsubstituted or via one or more R... 2 Replacement aryl compounds.

[0019] R 2 In each case, it may be the same or different and is F, CF3, or CN;

[0020] # indicates that A is CR b (where R) b When the group is a sub-formula T1 or a sub-formula T2, the sub-formula T1 or T2 group is connected to CR via a single bond. b The position of C in the middle;

[0021] Where at least one and at most four A's are N, or at least one R's b The group to be selected is one of the following: CF3, C(=O)R 1 CN, via one or more R 2 The substituted alkyl or aryl groups are derived from one or more R groups. 2 Substituted and optionally substituted with one or more unsubstituted alkyl groups and / or substituted with one or more unsubstituted or alkyl-substituted aryl groups, heteroaryl groups, which are unsubstituted or substituted with one or more R groups. 2 And / or substituted with one or more unsubstituted alkyl groups and / or substituted with one or more unsubstituted or alkyl-substituted aryl groups, and groups of formula T1 or formula T2:

[0022]

[0023] in

[0024] R N2 It is an alkyl group, unsubstituted or derived from one or more R groups. N3 Substituted aryl groups, or unsubstituted or via one or more R groups N3 Replacement of heteroaryl compounds.

[0025] R N3 It is alkyl, aryl, or heteroaryl.

[0026] # indicates that A is CR b (where R) b When the group is a sub-formula T1 or a sub-formula T2, the sub-formula T1 or T2 group is connected to CR via a single bond. b The position of C in the middle.

[0027] In a specific scheme, at least one and at most four A's are N, or at least one R's are N's. b The group to be selected is one of the following: CF3, C(=O)R 1 CN, via one or more R 2 Substituted alkyl or aryl groups, which are unsubstituted or have undergone one or more R... 2 Substituted and optionally substituted with one or more unsubstituted alkyl groups and / or substituted with one or more unsubstituted or alkyl-substituted aryl groups, heteroaryl groups, which are unsubstituted or substituted with one or more R groups. 2 And / or substituted with one or more unsubstituted alkyl groups and / or substituted with one or more unsubstituted or alkyl-substituted aryl groups, or groups of formula T1 or formula T2:

[0028]

[0029] in

[0030] R N2 It is an alkyl group, unsubstituted or derived from one or more R groups. N3 Substituted aryl groups, or unsubstituted or via one or more R groups N3 Replacement of heteroaryl compounds.

[0031] R N3 It is alkyl, aryl, or heteroaryl;

[0032] And among them, the rest are subject to the definitions given above.

[0033] In a specific scheme, R b As defined above, its condition is R b It is neither pyridine nor pyrimidine.

[0034] In one specific embodiment, the organic molecule comprises or is composed of a structure of formula A2.

[0035]

[0036] in:

[0037] R NIt is methyl, phenyl, methylbenzyl, mesitylene, naphthyl, biphenyl, naphthylphenyl, biphenyl or 2,4,6-triphenylphenyl;

[0038] R a In each case, they may be the same or different and are H, deuterium, alkyl or aryl;

[0039] R c In each case, it is the same or different and is CF3, C(=O)R 1 CN, via one or more R 2 Substituted alkyl groups, optionally substituted with one or more unsubstituted alkyl groups and / or substituted aryl groups substituted with one or more unsubstituted or alkyl-substituted aryl groups, unsubstituted or substituted with one or more R groups 2 And / or a heteroaryl group substituted with one or more unsubstituted alkyl groups and / or a heteroaryl group substituted with one or more unsubstituted or alkyl-substituted aryl groups, or a group of formula T1 or a group of formula T2:

[0040]

[0041] in

[0042] R N2 It is an alkyl group, unsubstituted or derived from one or more R groups. N3 Substituted aryl groups, or unsubstituted or via one or more R groups N3 Replacement of heteroaryl compounds.

[0043] R N3 It is alkyl, aryl, or heteroaryl.

[0044] # indicates that when R c When the group is a sub-formula T1 or a sub-formula T2, the sub-formula T1 or T2 group is attached to the position of carbazole via a single bond.

[0045] R d In each case, it is the same or different and is H, deuterium, CF3, C(=O)R 1 CN, unsubstituted or with one or more R 2 Substituted alkyl groups, unsubstituted alkyl groups, or alkyl groups with one or more R groups 2 and / or aryl groups substituted with one or more unsubstituted alkyl groups and / or aryl groups substituted with one or more unsubstituted or alkyl-substituted aryl groups, or aryl groups substituted with one or more R groups 2 And / or via one or more unsubstituted alkyl groups and / or via one or more unsubstituted or alkyl-substituted aryl groups, or groups of formula T1 or formula T2:

[0046]

[0047] in

[0048] R N2 It is an alkyl group, unsubstituted or derived from one or more R groups. N3 Substituted aryl groups, or unsubstituted or via one or more R groups N3 Replacement of heteroaryl compounds.

[0049] R N3 It is alkyl, aryl, or heteroaryl;

[0050] # indicates that when R d When the group is a sub-formula T1 or a sub-formula T2, the sub-formula T1 or T2 group is attached to the position of carbazole via a single bond.

[0051] And among them, the rest are subject to the definitions given above.

[0052] In further specific plans, R c In each case, the following groups are selected independently: CF3, C(=O)R 1 CN, via one or more R 2 Substituted alkyl groups, via one or more R 2 Substituted with and optionally substituted with one or more unsubstituted alkyl groups and / or substituted with one or more unsubstituted or alkyl-substituted aryl groups, unsubstituted or substituted with one or more R groups 2 And / or heteroaryl groups substituted with one or more unsubstituted alkyl groups and / or heteroaryl groups substituted with one or more unsubstituted or alkyl-substituted aryl groups, as well as groups of formula T1 or formula T2:

[0053]

[0054] in

[0055] R N2 It is an alkyl group, unsubstituted or derived from one or more R groups. N3 Substituted aryl groups, or unsubstituted or via one or more R groups N3 Replacement of heteroaryl compounds.

[0056] R N3 It is alkyl, aryl, or heteroaryl;

[0057] # indicates that when R c When the group is a sub-formula T1 or a sub-formula T2, the sub-formula T1 or T2 group is attached to the position of carbazole via a single bond;

[0058] And among them, the rest are subject to the definitions given above.

[0059] In further specific plans, R c As defined above, the condition is R c It is neither pyridine nor pyrimidine.

[0060] In further specific plans, R d In all cases, it is H.

[0061] In one specific embodiment, the organic molecule comprises or is composed of a structure of formula A3.

[0062]

[0063] in

[0064] R N It is methyl, phenyl, methylbenzyl, mesitylene, naphthyl, biphenyl, naphthylphenyl, biphenyl or 2,4,6-triphenylphenyl;

[0065] R a In each case, they may be the same or different and are H, deuterium, alkyl or aryl;

[0066] R c In each case, the following groups are selected independently: CF3, C(=O)R 1 CN, via one or more R 2 Substituted alkyl groups, optionally substituted with one or more unsubstituted alkyl groups and / or substituted aryl groups substituted with one or more unsubstituted or alkyl-substituted aryl groups, unsubstituted or substituted with one or more R groups 2 And / or heteroaryl groups substituted with one or more unsubstituted alkyl groups and / or heteroaryl groups substituted with one or more unsubstituted or alkyl-substituted aryl groups, as well as groups of formula T1 or formula T2:

[0067]

[0068] in

[0069] R N2 It is an alkyl group, unsubstituted or derived from one or more R groups. N3 Substituted aryl groups, or unsubstituted or via one or more R groups N3 Replacement of heteroaryl compounds.

[0070] R N3 It is alkyl, aryl, or heteroaryl.

[0071] # indicates that when R c When the group is a sub-formula T1 or a sub-formula T2, the sub-formula T1 or T2 group is attached to the position of carbazole via a single bond.

[0072] R d In each case, the groups that are the same or different and are independently selected from the following groups: H, deuterium, CF3, C(=O)R 1 CN, unsubstituted or with one or more R 2Substituted alkyl or aryl groups, which are unsubstituted or have undergone one or more R... 2 Substituted with and / or via one or more unsubstituted alkyl groups and / or via one or more unsubstituted or alkyl-substituted aryl groups, heteroaryl groups, wherein the aryl group is unsubstituted or via R 2 And / or substituted with one or more unsubstituted alkyl groups and / or substituted with one or more unsubstituted or alkyl-substituted aryl groups, and groups of formula T1 or formula T2:

[0073]

[0074] in

[0075] R N2 It is an alkyl group, unsubstituted or derived from one or more R groups. N3 Substituted aryl groups, or unsubstituted or via one or more R groups N3 Replacement of heteroaryl compounds.

[0076] R N3 It is alkyl, aryl, or heteroaryl;

[0077] # indicates that when R d When the group is a sub-formula T1 or a sub-formula T2, the sub-formula T1 or T2 group is attached to the position of carbazole via a single bond;

[0078] And among them, the rest are subject to the definitions given above.

[0079] In further specific plans, R c In each case, the following groups are selected independently: CF3, C(=O)R 1 CN, via one or more R 2 Substituted alkyl groups, via one or more R 2 Substituted and optionally substituted with one or more unsubstituted alkyl groups and / or substituted with one or more unsubstituted or alkyl-substituted aryl groups, unsubstituted or substituted with one or more R groups 2 and / or heteroaryl groups substituted with one or more unsubstituted alkyl groups and / or heteroaryl groups substituted with one or more unsubstituted or alkyl-substituted aryl groups, as well as groups of formula T1 or formula T2:

[0080]

[0081] in

[0082] R N2 It is an alkyl group, unsubstituted or derived from one or more R groups. N3 Substituted aryl groups, or unsubstituted or via one or more R groups N3 Replacement of heteroaryl compounds.

[0083] R N3It is alkyl, aryl, or heteroaryl;

[0084] # indicates that when R c When the group is a sub-formula T1 or a sub-formula T2, the sub-formula T1 or T2 group is attached to the position of carbazole via a single bond;

[0085] And among them, the rest are subject to the definitions given above.

[0086] In further specific plans, R c As defined above, the condition is R c It is neither pyridine nor pyrimidine.

[0087] In further specific plans, R d In all cases, it is H.

[0088] In a further specific embodiment, the organic molecule comprises or is composed of a structure of formula A4.

[0089]

[0090] in

[0091] R N It is methyl, phenyl, methylbenzyl, mesitylene, naphthyl, biphenyl, naphthylphenyl, biphenyl or 2,4,6-triphenylphenyl;

[0092] R a In each case, they may be the same or different and are H, deuterium, alkyl or aryl;

[0093] R c In each case, they are the same or different and are selected from the following groups: CF3, C(=O)R 1 CN, via one or more R 2 Substituted alkyl groups, via one or more R 2 Substituted and optionally substituted with one or more unsubstituted alkyl groups and / or substituted with one or more unsubstituted or alkyl-substituted aryl groups, unsubstituted or substituted with one or more R groups 2 and / or heteroaryl groups substituted with one or more unsubstituted alkyl groups and / or heteroaryl groups substituted with one or more unsubstituted or alkyl-substituted aryl groups, as well as groups of formula T1 or formula T2:

[0094]

[0095] R d In each case, they are either the same or different and are independently selected from the following groups: H, deuterium, CF3, C(=O)R 1 CN, unsubstituted or with one or more R 2Substituted alkyl or aryl groups, which are unsubstituted or have undergone one or more R... 2 Substituted with and / or via one or more unsubstituted alkyl groups and / or via one or more unsubstituted or alkyl-substituted aryl groups, heteroaryl groups, wherein the aryl group is unsubstituted or via R 2 And / or substituted with one or more unsubstituted alkyl groups and / or substituted with one or more unsubstituted or alkyl-substituted aryl groups, and groups of formula T1 or formula T2:

[0096]

[0097] in

[0098] R N2 It is an alkyl group, unsubstituted or derived from one or more R groups. N3 Substituted aryl groups, or unsubstituted or via one or more R groups N3 Replacement of heteroaryl compounds.

[0099] R N3 It is alkyl, aryl, or heteroaryl;

[0100] # indicates that when R c and / or R d When the group is a sub-formula T1 or a sub-formula T2, the sub-formula T1 or T2 group is attached to the position of carbazole via a single bond;

[0101] And among them, the rest are subject to the definitions given above.

[0102] In further specific plans, R c In each case, the following groups are selected independently: CF3, C(=O)R 1 CN, via one or more R 2 Substituted alkyl groups, via one or more R 2 Substituted and optionally substituted with one or more unsubstituted alkyl groups and / or substituted with one or more unsubstituted or alkyl-substituted aryl groups, unsubstituted or substituted with one or more R groups 2 and / or heteroaryl groups substituted with one or more unsubstituted alkyl groups and / or heteroaryl groups substituted with one or more unsubstituted or alkyl-substituted aryl groups, as well as groups of formula T1 or formula T2:

[0103]

[0104] Among them, R N2 It is an alkyl group, unsubstituted or derived from one or more R groups. N3 Substituted aryl groups, or unsubstituted or via one or more R groups N3 Replacement of heteroaryl compounds.

[0105] R N3It is alkyl, aryl, or heteroaryl;

[0106] # indicates that when R c When the group is a sub-formula T1 or a sub-formula T2, the sub-formula T1 or T2 group is attached to the position of carbazole via a single bond;

[0107] And among them, the rest are subject to the definitions given above.

[0108] In further specific plans, R c As defined above, the condition is R c It is neither pyridine nor pyrimidine.

[0109] In further specific plans, R d In all cases, it is H.

[0110] In a further specific embodiment, the organic molecule comprises or is composed of the structure of formula A5.

[0111]

[0112] in:

[0113] R N It is methyl, phenyl, methylbenzyl, mesitylene, naphthyl, biphenyl, naphthylphenyl, biphenyl or 2,4,6-triphenylphenyl;

[0114] R a In each case, they may be the same or different and are H, deuterium, alkyl or aryl;

[0115] R c In each case, it is the same or different and is CF3, C(=O)R 1 CN, via one or more R 2 Substituted alkyl groups, via one or more R 2 Substituted and optionally substituted with one or more unsubstituted alkyl groups and / or substituted with one or more unsubstituted or alkyl-substituted aryl groups, unsubstituted or substituted with one or more R groups 2 And / or via one or more unsubstituted alkyl groups and / or via one or more unsubstituted or alkyl-substituted aryl groups, or groups of formula T1 or formula T2:

[0116]

[0117] in

[0118] R N2 It is an alkyl group, unsubstituted or derived from one or more R groups. N3 Substituted aryl groups, or unsubstituted or via one or more R groups N3 Replacement of heteroaryl compounds.

[0119] R N3 It is alkyl, aryl, or heteroaryl;

[0120] # indicates that when R c When the group is a sub-formula T1 or a sub-formula T2, the sub-formula T1 or T2 group is attached to the position of carbazole via a single bond.

[0121] R d In each case, it is the same or different and is H, deuterium, CF3, C(=O)R 1 CN, unsubstituted or with one or more R 2 Substituted alkyl groups, unsubstituted alkyl groups, or alkyl groups with one or more R groups 2 and / or aryl groups substituted with one or more unsubstituted alkyl groups and / or aryl groups substituted with one or more unsubstituted or alkyl-substituted aryl groups, unsubstituted or substituted with one or more R groups 2 And / or via one or more unsubstituted alkyl groups and / or via one or more unsubstituted or alkyl-substituted aryl groups, or groups of formula T1 or formula T2:

[0122]

[0123] Where R N2 It is an alkyl group, unsubstituted or derived from one or more R groups. N3 Substituted aryl groups, or unsubstituted or via one or more R groups N3 Replacement of heteroaryl compounds.

[0124] R N3 It is alkyl, aryl, or heteroaryl.

[0125] # indicates that when R d When the group is a sub-formula T1 or a sub-formula T2, the sub-formula T1 or T2 group is attached to the position of carbazole via a single bond.

[0126] In further specific plans, R c In each case, the following groups are selected independently: CF3, C(=O)R 1 CN, via one or more R 2 Substituted alkyl groups, via one or more R 2 Substituted and optionally substituted with one or more unsubstituted alkyl groups and / or substituted with one or more unsubstituted or alkyl-substituted aryl groups, unsubstituted or substituted with one or more R groups 2 and / or heteroaryl groups substituted with one or more unsubstituted alkyl groups and / or heteroaryl groups substituted with one or more unsubstituted or alkyl-substituted aryl groups, as well as groups of formula T1 or formula T2:

[0127]

[0128] in

[0129] R N2 It is an alkyl group, unsubstituted or derived from one or more R groups. N3 Substituted aryl groups, or unsubstituted or via one or more R groups N3 Replacement of heteroaryl compounds.

[0130] R N3 It is alkyl, aryl, or heteroaryl;

[0131] # indicates that when R c When the group is a sub-formula T1 or a sub-formula T2, the sub-formula T1 or T2 group is attached to the position of carbazole via a single bond;

[0132] And among them, the rest are subject to the definitions given above.

[0133] In further specific plans, R c As defined above, the condition is R c It is neither pyridine nor pyrimidine.

[0134] In further specific plans, R d In all cases, it is H.

[0135] In one specific embodiment, the organic molecule has the structure of formula A6.

[0136]

[0137] in

[0138] R N It is methyl, phenyl, methylbenzyl, mesitylene, naphthyl, biphenyl, naphthylphenyl, biphenyl or 2,4,6-triphenylphenyl;

[0139] R a In each case, they may be the same or different and are H, deuterium, alkyl or aryl;

[0140] R c In each case, the following groups are selected independently: CF3, C(=O)R 1 CN, via one or more R 2 Substituted alkyl groups, via one or more R 2 Substituted and optionally substituted with one or more unsubstituted alkyl groups and / or substituted with one or more unsubstituted or alkyl-substituted aryl groups, unsubstituted or substituted with one or more R groups 2 And / or via one or more unsubstituted alkyl groups and / or via one or more unsubstituted or alkyl-substituted aryl groups, or groups of formula T1 or formula T2:

[0141]

[0142] in

[0143] R N2 It is an alkyl group, unsubstituted or derived from one or more R groups. N3 Substituted aryl groups, or unsubstituted or via one or more R groups N3 Replacement of heteroaryl compounds.

[0144] R N3 It is alkyl, aryl, or heteroaryl;

[0145] # indicates that when R c When the group is a sub-formula T1 or a sub-formula T2, the sub-formula T1 or T2 group is attached to the position of carbazole via a single bond.

[0146] R d In each case, the following groups are selected independently: H, deuterium, CF3, C(=O)R 1 CN, unsubstituted or with one or more R 2 Substituted alkyl groups, unsubstituted alkyl groups, or alkyl groups with one or more R groups 2 Substituted with and / or via one or more unsubstituted alkyl groups and / or via one or more unsubstituted or alkyl-substituted aryl groups, unsubstituted or R 2 and / or heteroaryl groups substituted with one or more unsubstituted alkyl groups and / or heteroaryl groups substituted with one or more unsubstituted or alkyl-substituted aryl groups, as well as groups of formula T1 or formula T2:

[0147]

[0148] in

[0149] R N2 It is an alkyl group, unsubstituted or derived from one or more R groups. N3 Substituted aryl groups, or unsubstituted or via one or more R groups N3 Replacement of heteroaryl compounds.

[0150] R N3 It is alkyl, aryl, or heteroaryl;

[0151] # indicates that when R d When the group is a sub-formula T1 or a sub-formula T2, the sub-formula T1 or T2 group is attached to the position of carbazole via a single bond;

[0152] And among them, the rest are subject to the definitions given above.

[0153] In further specific plans, R c In each case, the following groups are selected independently: CF3, C(=O)R 1CN, via one or more R 2 Substituted alkyl groups, via one or more R 2 Substituted and optionally substituted with one or more unsubstituted alkyl groups and / or substituted with one or more unsubstituted or alkyl-substituted aryl groups, unsubstituted or substituted with one or more R groups 2 and / or heteroaryl groups substituted with one or more unsubstituted alkyl groups and / or heteroaryl groups substituted with one or more unsubstituted or alkyl-substituted aryl groups, as well as groups of formula T1 or formula T2:

[0154]

[0155] in

[0156] R N2 It is an alkyl group, unsubstituted or derived from one or more R groups. N3 Substituted aryl groups, or unsubstituted or via one or more R groups N3 Replacement of heteroaryl compounds.

[0157] R N3 It is alkyl, aryl, or heteroaryl;

[0158] # indicates that when R c When the group is a sub-formula T1 or a sub-formula T2, the sub-formula T1 or T2 group is attached to the position of carbazole via a single bond;

[0159] And among them, the rest are subject to the definitions given above.

[0160] In further specific plans, R c As defined above, the condition is R c It is neither pyridine nor pyrimidine.

[0161] In further specific plans, R d In all cases, it is H.

[0162] In a further specific embodiment, the organic molecule comprises or is composed of a structure of formula A7.

[0163]

[0164] in

[0165] R N It is methyl, phenyl, methylbenzyl, mesitylene, naphthyl, biphenyl, naphthylphenyl, biphenyl or 2,4,6-triphenylphenyl;

[0166] R a In each case, they may be the same or different and are H, deuterium, alkyl or aryl;

[0167] R cIn each case, the following groups are selected independently: CF3, C(=O)R 1 CN, via one or more R 2 Substituted alkyl groups, via one or more R 2 Substituted and optionally substituted with one or more unsubstituted alkyl groups and / or substituted with one or more unsubstituted or alkyl-substituted aryl groups, unsubstituted or substituted with one or more R groups 2 and / or heteroaryl groups substituted with one or more unsubstituted alkyl groups and / or heteroaryl groups substituted with one or more unsubstituted or alkyl-substituted aryl groups, as well as groups of formula T1 or formula T2:

[0168]

[0169] in

[0170] R N2 It is an alkyl group, unsubstituted or derived from one or more R groups. N3 Substituted aryl groups, or unsubstituted or via one or more R groups N3 Substituted heteroaryl groups;

[0171] R N3 It is alkyl, aryl, or heteroaryl;

[0172] # indicates that when R c When the group is a sub-formula T1 or a sub-formula T2, the sub-formula T1 or T2 group is attached to the position of carbazole via a single bond.

[0173] R d In each case, they are either the same or different and are independently selected from the following groups: H, deuterium, CF3, C(=O)R 1 CN, unsubstituted or with one or more R 2 Substituted alkyl groups, unsubstituted alkyl groups, or alkyl groups with one or more R groups 2 and / or aryl groups substituted with one or more unsubstituted alkyl groups and / or aryl groups substituted with one or more unsubstituted or alkyl-substituted aryl groups, unsubstituted or R 2 and / or heteroaryl groups substituted with one or more unsubstituted alkyl groups and / or heteroaryl groups substituted with one or more unsubstituted or alkyl-substituted aryl groups, as well as groups of formula T1 or formula T2:

[0174]

[0175] in

[0176] R N2 It is an alkyl group, unsubstituted or derived from one or more R groups. N3 Substituted aryl groups, or unsubstituted or via one or more R groups N3 Substituted heteroaryl groups;

[0177] R N3 It is alkyl, aryl, or heteroaryl;

[0178] # indicates that when R d When the group is a sub-formula T1 or a sub-formula T2, the sub-formula T1 or T2 group is attached to the position of carbazole via a single bond;

[0179] And among them, the rest are subject to the definitions given above.

[0180] In further specific plans, R c In each case, the following groups are selected independently: CF3, C(=O)R 1 CN, via one or more R 2 Substituted alkyl groups, via one or more R 2 Substituted and optionally substituted with one or more unsubstituted alkyl groups and / or substituted with one or more unsubstituted or alkyl-substituted aryl groups, unsubstituted or substituted with one or more R groups 2 and / or heteroaryl groups substituted with one or more unsubstituted alkyl groups and / or heteroaryl groups substituted with one or more unsubstituted or alkyl-substituted aryl groups, as well as groups of formula T1 or formula T2:

[0181]

[0182] in

[0183] R N2 It is an alkyl group, unsubstituted or derived from one or more R groups. N3 Substituted aryl groups, or unsubstituted or via one or more R groups N3 Substituted heteroaryl groups;

[0184] R N3 It is alkyl, aryl, or heteroaryl;

[0185] # indicates that when R c When the group is a sub-formula T1 or a sub-formula T2, the sub-formula T1 or T2 group is attached to the position of carbazole via a single bond;

[0186] And among them, the rest are subject to the definitions given above.

[0187] In further specific plans, R c As defined above, the condition is R c It is neither pyridine nor pyrimidine.

[0188] In further specific plans, R d In all cases, it is H.

[0189] A specific scheme relates to an organic molecule of the formula A1, A2, A3, A4, A5, A6 or A7 having at least one CN group.

[0190] In the context of this invention, aryl (which may be substituted by the aforementioned groups in various cases and may be linked to the aromatic system via any desired position) is understood to mean derived from the following groups: benzene, naphthalene, anthracene and phenanthrene.

[0191] Illustratively, aryl groups substituted with phenyl or alkyl groups, particularly toluene, ethylbenzene, cumene, tert-butylbenzene, isobutylbenzene, o-xylene (1,2-xylene), m-xylene (1,3-xylene), p-xylene (1,4-xylene), 1,5-xylene, 1,2-diethylbenzene, 1,3-diethylbenzene, 1,4-diethylbenzene, 1,5-diethylbenzene, 1,2-diisopropylbenzene, 1,3-diisopropylbenzene, 1,4-diisopropylbenzene, 1,5-diisopropylbenzene, 1,2-di-tert-butylbenzene, 1,3-di-tert-butylbenzene, 1,4-di-tert-butylbenzene, 1,5-di-tert-butylbenzene, and mesitylene (1,3,5-trimethylbenzene). (1,3,5-trimethylbenzene), 1,3,5-triethylbenzene, 1,3,5-triisopropylbenzene, 1,3,5-tri-tert-butylbenzene, phenylbenzene, 1,2-diphenylbenzene, 1,3-diphenylbenzene, 1,4-diphenylbenzene, and 1,3,5-triphenylbenzene.

[0192] In the context of this invention, heteroaryl groups (which may be substituted by the aforementioned groups in various cases and may be linked to the heteroaromatic system via any desired position) are understood to mean those derived from the following groups: pyridine, pyridazine (1,2-diazine), pyrimidine (1,3-diazine), pyrazine (1,4-diazine), 1,3,5-triazine, acridine, quinoline, isoquinoline, quinoxaline, and naphthidine.

[0193] Illustrative heteroaryl groups substituted with phenyl or alkyl groups, particularly 2-methylpyridine (2-methylpyridine), 3-methylpyridine (3-methylpyridine), 4-methylpyridine (4-methylpyridine), 2-ethylpyridine, 3-ethylpyridine, 4-ethylpyridine, 2-isopropylpyridine, 3-isopropylpyridine, 4-isopropylpyridine, 2-tert-butylpyridine, 3-tert-butylpyridine, 4-tert-butylpyridine, 2-isobutylpyridine, 3-isobutylpyridine, 4-isobutylpyridine, 2,3-dimethylpyridine, 2,4-dimethylpyridine, 2,5-dimethylpyridine, 2,6-dimethylpyridine Pyridine, 2,3-diethylpyridine, 2,4-diethylpyridine, 2,5-diethylpyridine, 2,6-diethylpyridine, 2,3-diisopropylpyridine, 2,4-diisopropylpyridine, 2,5-diisopropylpyridine, 2,6-diisopropylpyridine, 2,3-di-tert-butylpyridine, 2,4-di-tert-butylpyridine, 2,5-di-tert-butylpyridine, 2,6-di-tert-butylpyridine, 2,4,6-trimethylpyridine, 2,4,6-triethylpyridine, 2,4,6-triisopropylpyridine, 2,4,6-tri-tert-butylpyridine, 2-methylpyrimidine 4-Methylpyrimidine, 5-methylpyrimidine, 2,4-dimethylpyrimidine, 2,5-dimethylpyrimidine, 4,5-dimethylpyrimidine, 4,6-dimethylpyrimidine, 2,4-diethylpyrimidine, 2,5-diethylpyrimidine, 4,5-diethylpyrimidine, 4,6-diethylpyrimidine, 2,4-diisopropylpyrimidine, 2,5-diisopropylpyrimidine, 4,5-diisopropylpyrimidine, 4,6-diisopropylpyrimidine, 2,4-di-tert-butylpyrimidine, 2,5-di-tert-butylpyrimidine, 4,5-di-tert-butylpyrimidine, 4,6-di-tert-butylpyrimidine, 2,4,5- Trimethylpyrimidine, 2,4,5-triethylpyrimidine, 2,4,5-triisopropylpyrimidine, 2,4,5-tri-tert-butylpyrimidine, 2,4,5-trimethylpyrimidine, 2,4,6-triethylpyrimidine, 2,4,6-triisopropylpyrimidine, 2,4,6-tri-tert-butylpyrimidine, 4,5,6-trimethylpyrimidine, 4,5,6-triethylpyrimidine, 4,5,6-triisopropylpyrimidine, 4,5,6-tri-tert-butylpyrimidine, 4,5,6-trimethylpyrimidine, 2,4-dimethyl-1,3,5-triazine, and 2,4-diphenyl-1,3,5-triazine.

[0194] In the context of this invention, alkyl (where individual hydrogen atoms may optionally be substituted by the aforementioned groups) is understood to mean, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, 2-methylbutyl, n-pentyl, sec-pentyl, tert-pentyl, 2-pentyl, neopentyl, cyclopentyl, n-hexyl, sec-hexyl, tert-hexyl, 2-hexyl, 3-hexyl, neohexyl, cyclohexyl, 1-methylcyclopentyl, 2-methylpentyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, cycloheptyl, 1-methylcyclohexyl group.

[0195] R N The groups can be connected at any position. In the context of this invention, biphenyl is understood to mean, for example, ortho-biphenyl, para-biphenyl, and meta-biphenyl; triphenyl means 1,2-diphenylphenyl, 1,3-diphenylphenyl, and 1,4-diphenylphenyl; and naphthylphenyl means, for example, ortho-naphthylphenyl, meta-naphthylphenyl, and para-naphthylphenyl. The illustrative and thus non-limiting specific embodiments are as follows:

[0196]

[0197]

[0198] The molecules according to the present invention have high photoluminescence quantum yield and short exciton lifetime, and are therefore advantageous emitter materials for blue OLEDs.

[0199] One specific aspect of the present invention relates to an organic molecule having an emission maximum value between 420 and 490 nm, more preferably between 430 and 470 nm, and even more preferably between 440 and 460 nm.

[0200] One specific aspect of this invention relates to an organic molecule having an emission lifetime of no more than 150 µs, particularly no more than 100 µs, no more than 50 µs, or no more than 10 µs, and / or having a main emission band with a half-height width of less than 120 nm, particularly less than 100 nm, less than 80 nm, or less than 60 nm, and / or having a photoluminescence quantum yield (PLQY) of greater than 30%, particularly greater than 35%, greater than 40%, greater than 45%, greater than 50%, or greater than 60%, and / or having a ΔE(S1-T1) value of no more than 5000 cm⁻¹ between the lowest excited singlet state (S1) and the triplet state (T1) below it. -1 Especially those not exceeding 3000 cm -1 or not greater than 1500 cm -1 Or 1000 cm -1 .

[0201] More particularly, the molecules according to the present invention have a Blue Material Index (BMI) greater than 150, especially greater than 200, greater than 250, or greater than 300 (which is the PLQY (in percentage) of the light emitted by the molecules according to the present invention) and its CIE. y (quotient of color coordinates).

[0202] The value of ΔE(S1-T1) can be determined by quantum mechanical calculation using a computer program known in the art (e.g., using the Turbomole program that performs TD-DFT calculations and references CC2 operations), or by experimental means as further explained below.

[0203] The energy difference ΔE(S1-T1) can be approximated by quantum mechanics through a so-called exchange integral multiplied by a factor of 2. Its value depends directly on the overlap of molecular orbitals. These molecular orbitals are distributed in different spatial regions (partially delocalized to...). or (Molecular orbitals). This refers to electronic transitions between different molecular orbitals that represent so-called charge transfer (CT) transitions. The smaller the overlap of the aforementioned molecular orbitals, the more significant the electronic charge transfer characteristic. This is therefore related to a decrease in the exchange integral, and thus to a decrease in the energy difference ΔE(S1-T1).

[0204] The value of ΔE(S1-T1) can be determined experimentally as follows:

[0205] For a given organic molecule, the band gap ΔE(S1-T1) = ΔE can be determined in a simple way using equation (1) provided below. Rearranging, we get:

[0206]

[0207] For the strength Int(S1) S0) and Int(T1) The measurement of S0 can be performed using any commercial spectrophotometer. The (logarithmic) intensity ratio measured at different temperatures is ln{Int(S1) S0) / Int(T1 A graph plotting S0)} relative to the reciprocal of the absolute temperature T typically yields a straight line. Measurements are generally taken within a temperature range from room temperature (300 K) to 77 K or 4.2 K, regulated using a cryostat. The intensity is determined by the (corrected) spectrum, where Int(S1) S0) and Int(T1) S0) represents the integrated fluorescence and phosphorus spectral band intensities, respectively, which can be determined using a program integrated into the spectrophotometer. Each transition (band intensity) is readily identifiable because triplet bands are located at lower energies than singlet bands and their intensity increases with decreasing temperature. Measurements are taken in an oxygen-free dilution solution (approximately 10...). -2The application can be performed in solutions (mol / L), on thin films composed of the corresponding molecules, or on films doped with the corresponding molecules. If using a solution as a sample, it is recommended to use a solvent or solvent mixture that forms a glass at low temperatures, such as 2-methyl-THF, THF (tetrahydrofuran), or aliphatic hydrocarbons. If using a film as a sample, a matrix with singlet and triplet energies much larger than those of organic emitter molecules is suitable, such as PMMA (polymethyl methacrylate). This film can be applied by solution.

[0208] The slope of the straight line is -ΔE / k B Where k B = 1.380 10 -23 JK -1 = 0.695 cm -1 K -1 It may directly determine the band gap.

[0209] Similarly, it is possible to determine the value of ΔE(S1-T1) by measuring the temperature dependence of the emission decay time.

[0210] The ΔE(S1-T1) value can also be estimated by recording fluorescence and phosphorescence spectra at low temperatures (e.g., 77K or 4.2K using a cryostat). The ΔE(S1-T1) value is approximately equivalent to the energy difference between the high-energy rise edges of the fluorescence / phosphorescence spectral bands.

[0211] The more pronounced the CT characteristics of an organic molecule, the greater the change in electronic transition energy as a function of solvent polarity. Therefore, even a significant polarity dependence of emission energy suggests the existence of a small ΔE(S1-T1) value.

[0212] In a further aspect, the present invention relates to the use of the organic molecule as a light emitter or as a host material in an organic optoelectronic device, particularly wherein the organic optoelectronic device is selected from the group consisting of:

[0213] Organic light-emitting diodes (OLEDs),

[0214] • Photoluminescent electrochemical cells

[0215] • OLED sensors, especially in gas and vapor sensors that are not hermetically shielded from external elements.

[0216] Organic diodes,

[0217] Organic solar cells,

[0218] Organic transistors,

[0219] • Organic field-effect transistor,

[0220] Organic lasers, and

[0221] • Down-conversion element.

[0222] In a further aspect, the present invention relates to compositions comprising or consisting of the following components:

[0223] (a) At least one organic molecule according to the invention, particularly as an emitter and / or host, and

[0224] (b) at least one (i.e., one, two, or more) emitter and / or host material other than the organic molecule according to the invention, and

[0225] (c) Optionally at least one dye and / or at least one organic solvent.

[0226] In one specific embodiment, the composition according to the invention comprises an organic molecule according to the invention and one or more host materials. The host materials, in particular, have triplet (T1) and singlet (S1) energy levels located at higher energies than the triplet (T1) and singlet (S1) energy levels of the organic molecule according to the invention. In one specific embodiment, the composition, like the organic molecule according to the invention, comprises electron-dominant and hole-dominant host materials. The highest occupied orbital (HOMO) and lowest unoccupied orbital (LUMO) of the hole-dominant host material are located at higher energies than the HOMO and LUMO of the electron-dominant host material. The HOMO of the hole-dominant host material is located at lower energies than the HOMO of the organic molecule according to the invention, while the LUMO of the electron-dominant host material is located at higher energies than the LUMO of the organic molecule according to the invention. To avoid the formation of an excited complex between the emitter and the host materials, these materials should be selected such that the band gap between the orbitals is small. The gap between the LUMO of the electron-dominant host material and the LUMO of the organic molecule according to the invention is particularly less than 0.5 eV, more preferably less than 0.3 eV, and even more preferably less than 0.2 eV. The gap between the HOMO of the hole-dominant host material and the HOMO of the organic molecule according to the invention is particularly less than 0.5 eV, more preferably less than 0.3 eV, and even more preferably less than 0.2 eV.

[0227] In a further aspect, the present invention relates to organic optoelectronic devices comprising organic molecules according to the invention or compositions according to the invention. Such organic optoelectronic devices are particularly in the form of devices selected from the group consisting of: organic light-emitting diodes (OLEDs); light-emitting electrochemical cells; OLED sensors, especially gas and vapor sensors not hermetically shielded from external sources; organic diodes; organic solar cells; organic transistors; organic field-effect transistors; organic lasers; and down-conversion elements.

[0228] An organic optoelectronic device having the following components is a further specific embodiment of the present invention:

[0229] - substrate,

[0230] - Anode and

[0231] - Cathode, wherein the anode or cathode has been applied to the substrate, and

[0232] - At least one light-emitting layer disposed between the anode and the cathode and containing organic molecules according to the invention.

[0233] In one specific embodiment, the optoelectronic device is an OLED. A typical OLED has, for example, the following layer structure:

[0234] 1. Substrate (carrier material)

[0235] 2. Anode

[0236] 3. Hole Injection Layer (HIL)

[0237] 4. Hole Transport Layer (HTL)

[0238] 5. Electron blocking layer (EBL)

[0239] 6. Emitting Layer (EML)

[0240] 7. Hole Blocking Layer (HBL)

[0241] 8. Electron Transport Layer (ETL)

[0242] 9. Electron Injection Layer (EIL)

[0243] 10. Cathode.

[0244] The layers mentioned here exist only in an optional manner. Furthermore, two or more of these layers may be merged. And each layer may appear more than once in a component.

[0245] In one specific embodiment, at least one electrode in the organic component is translucent. "Translucent" here refers to a layer that is transparent to visible light. This translucent layer may be clear and transparent, i.e., transparent, or it may at least partially absorb light and / or partially scatter light, such that the translucent layer may, for example, have a diffuse or milky appearance. More specifically, the layer referred to here as translucent is clearly transparent, such that, in particular, the light absorption coefficient is as low as possible.

[0246] In a further specific embodiment, the organic component, particularly the OLED, has an inverted structure. The inverted structure is characterized by the cathode being mounted on the substrate, while the other layers are applied in a correspondingly inverted manner.

[0247] 1. Substrate (carrier material)

[0248] 2. Cathode

[0249] 3. Electron Injection Layer (EIL)

[0250] 4. Electron Transport Layer (ETL)

[0251] 5. Hole Blocking Layer (HBL)

[0252] 6. Emission Layer / Emitting Layer (EML)

[0253] 7. Electron blocking layer (EBL)

[0254] 8. Hole Transport Layer (HTL)

[0255] 9. Hole Injection Layer (HIL)

[0256] 10. Anode

[0257] The layers mentioned here exist only in an optional manner. Furthermore, two or more of these layers may be merged. And each layer may appear more than once in a component.

[0258] In one specific embodiment, in an inverted OLED, the anode layer, such as an ITO (indium tin oxide) layer, in a typical structure is connected as a cathode.

[0259] In a further specific embodiment, the organic component, particularly the OLED, has a stacked structure. Here, the individual OLEDs are arranged one on top of another instead of being placed side-by-side as usual. This stacked structure allows for the generation of mixed light. For example, this structure can be used to generate white light, typically manufactured by combining light emitted from blue, green, and red emitters to form the entire visible spectrum. Furthermore, it can achieve a significantly longer lifetime than standard OLEDs with roughly the same efficiency and luminosity. Optionally, a so-called charge-generating layer (CGL) may be used between the two OLEDs in relation to the stacked structure. This consists of an n-doped layer and a p-doped layer, with the n-doped layer typically applied closer to the anode.

[0260] In one specific embodiment—referred to as a tandem OLED—two or more emitting layers exist between the anode and cathode. In one embodiment, three emitting layers are arranged one on top of another, with one emitting layer emitting red light, one emitting green light, and one emitting blue light, and optionally, charge-generating, blocking, or transporting layers are further applied between the emitting layers. In a further embodiment, the emitting layers are applied in a directly adjacent manner. In a further embodiment, a charge-generating layer is present between the emitting layers in each case. Furthermore, in OLEDs, directly adjacent emitting layers and emitting layers separated by charge-generating layers may be combined.

[0261] Encapsulation may also be arranged on the electrodes and organic layer. Encapsulation may take the form of, for example, a glass cover or a thin-film encapsulation.

[0262] The carrier material used in optoelectronic devices may be, for example, glass, quartz, plastic, metal, silicon wafer, or any other suitable solid or flexible (optionally transparent) material.

[0263] The carrier material used may include, for example, one or more materials in the form of layers, films, sheets or laminates.

[0264] The anode used in optoelectronic devices can be, for example, a transparent conductive metal oxide, such as ITO (indium tin oxide), zinc oxide, tin oxide, cadmium oxide, titanium oxide, indium oxide, or aluminum zinc oxide (AZO), Zn2SnO4, CdSnO3, ZnSnO3, MgIn2O4, GaInO3, Zn2In2O5, or In4Sn3O 12 Or a mixture of different transparent conductive oxides.

[0265] The HIL material used can be, for example, PEDOT:PSS (poly-3,4-ethylenedioxythiophene):polystyrene sulfonic acid), PEDOT (poly-3,4-ethylenedioxythiophene), m-MTDATA (4,4',4''-tris[phenyl(m-tolyl)amino]triphenylamine), spiro-TAD (2,2',7,7'-tetra(N,N-diphenylamino)-9,9-spirodifluorene), DNTPD (4,4'-bis[N-[4-{N,N-bis(3-methylphenyl)amino}phenyl]-N-phenylamino]biphenyl), 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-diphenylamino)phenyl]benzene), MeO-TPD (N,N,N',N'-tetra(4-methoxyphenyl)benzene), HAT-CN (1,4,5,8,9,11-hexaazatriphenylhexacarboxynitrile), or spiro-NPD (N,N'-diphenyl-N,N'-bis-(1-naphthyl)-9,9'-spirodifluorene-2,7-diamine). As an example, the layer thickness is 10-80 nm. Furthermore, small molecules (e.g., copper phthalocyanine (CuPc, e.g., 10 nm thick)) or metal oxides may be used, with MoO3 and V2O5 as examples.

[0266] The HTL material used can be a tertiary amine, a carbazole derivative, poly(ethylenedioxythiophene) doped with polystyrene sulfonate, polyaniline doped with camphor sulfonate, poly-TPD (poly(4-butylphenyldiphenylamine), [α]-NPD (poly(4-butylphenyldiphenylamine)), TAPC (4,4'-cyclohexylenebis[N,N-bis(4-methylphenyl)aniline]), TCTA (tris(4-carbazole-9-ylphenyl)amine), 2-TNATA (4,4',4''-tris[2-naphthyl(phenyl)amino]triphenylamine), spiro-TAD, DNTPD, NPB, NPNPB, MeO-TPD, HAT-CN, or TrisPcz (9,9'-diphenyl-6-(9-phenyl-9H-carbazole-3-yl)-9H,9'H-3,3'-bicarbazole). As an example, the layer thickness is 10-100 nm.

[0267] HTLs may have a p-doped layer containing inorganic or organic dopants within an organic hole-conducting matrix. The inorganic dopants used may be, for example, transition metal oxides such as vanadium oxide, molybdenum oxide, or tungsten oxide. The organic dopants used may be, for example, tetrafluorotetracyanoquinone dimethyl ether (F4-TCNQ), copper pentafluorobenzoate (Cu(I)pFBz), or transition metal complexes. As an example, the layer thickness is from 10 nm to 100 nm.

[0268] The electron blocking layer material used can be, for example, mCP (1,3-bis(carbazole-9-yl)phenyl), TCTA, 2-TNATA, mCBP (3,3-bis(9H-carbazole-9-yl)biphenyl), tri-Pcz (9,9'-diphenyl-6-(9-phenyl-9H-carbazole-3-yl)-9H,9'H-3,3'-bicarbazole), CzSi (9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole), or DCB (N,N'-dicarbazole-1,4-xylene). As an example, the layer thickness is from 10 nm to 50 nm.

[0269] The emitter layer (EML) or emitter layer is composed of or contains the following components: emitter material or a mixture containing at least two emitter materials, and optionally one or more host materials. Suitable host materials are, for example, mCP, TCTA, 2-TNATA, mCBP, CBP (4,4'-bis-(N-carbazolyl)biphenyl), Sif87 (dibenzo[b,d]thiophene-2-yltriphenylsilane), Sif88 (dibenzo[b,d]thiophene-2-yl)diphenylsilane), or DPEPO (bis[2-((sideoxy)diphenylphosphine)phenyl] ether). For emitter materials emitting green or red light, or mixtures containing at least two emitter materials, standard matrix materials, such as CBP, are suitable. Regarding the blue emitter material or a mixture containing at least two emitter materials, UHG matrix materials (ultra-high bandgap materials) may be used (see, for example, ME Thompson et al., Chem. Mater. 2004, 16, 4743) or other so-called wide-bandgap matrix materials. As an example, the layer thickness ranges from 10 nm to 250 nm.

[0270] Hole-blocking layers (HBLs) may include, for example, BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), bis(2-methyl-8-hydroxyquinolinato)-(4-phenylphenolato)aluminium(III) (BAlq), Nbphen (2,9-bis(naphthyl-2-yl)-4,7-diphenyl-1,10-phenanthroline), Alq3 (aluminum(8-hydroxyquinolinato)), TSPO1 (diphenyl-4-triphenylsilylphenylphosphine oxide), or TCB / TCP (1,3,5-tris(N-carbazolyl)benzene / 1,3,5-tris(carbazolyl)-9-yl)benzene). As an example, the layer thickness is from 10 nm to 50 nm.

[0271] Electron transport layer (ETL) may include, for example, AlQ3, TSPO1, BPyTP2 (2,7-bis(2,2'-bipyridin-5-yl)triphenyl), Sif87, Sif88, BmPyPhB (1,3-bis[3,5-bis(pyridin-3-yl)phenyl]benzene), or BTB (4,4'-bis-[2-(4,6-diphenyl-1,3,5-triazinyl)... Materials based on ]-1,1'-biphenyl. As an example, the layer thickness ranges from 10 nm to 200 nm.

[0272] Materials used for the thin electron injection layer (EIL) can be, for example, CsF, LiF, 8-hydroxyquinolinolatolithium (Liq), Li2O, BaF2, MgO, or NaF.

[0273] The material used for the cathode layer can be a metal or alloy, such as Al, Al > AlF, Ag, Pt, Au, Mg, or Ag:Mg. Typical layer thicknesses range from 100 nm to 200 nm. In particular, one or more metals stable in air and / or through self-passivation (e.g., by the formation of a thin protective oxide layer) are used.

[0274] Suitable materials for encapsulation include, for example, aluminum oxide, vanadium oxide, zinc oxide, zirconium oxide, titanium oxide, hafnium oxide, lanthanum oxide, and tantalum oxide.

[0275] In one specific embodiment of the organic optoelectronic device according to the present invention, the organic molecule according to the present invention is used as the emitting material in the light emitting layer (EML), wherein it is used in the form of a pure layer or in combination with one or more host materials.

[0276] One specific aspect of this invention relates to an organic optoelectronic device, which operates at 1000 cd / m². 2 It has an external quantum efficiency (EQE) greater than 5%, especially greater than 8%, especially greater than 10%, or greater than 13%, or greater than 16%, and especially greater than 20%, and / or has an emission maximum at wavelengths between 420 nm and 500 nm, especially between 430 nm and 490 nm, or between 440 nm and 480 nm, and especially between 450 nm and 470 nm, and / or has an emission maximum at 500 cd / m 2 The LT80 values ​​are greater than 30h, especially greater than 70h, or greater than 100h, or greater than 150h, and especially greater than 200h.

[0277] In a further specific embodiment of the light-emitting layer in an optical light-emitting device, particularly an OLED, the mass ratio of the organic molecules according to the invention in the emitter layer (EML) is between 1% and 80%. In a specific embodiment of the organic optoelectronic device according to the invention, the light-emitting layer is applied to a substrate, preferably with an anode and a cathode applied to the substrate, and the light-emitting layer applied between the anode and the cathode.

[0278] In one specific embodiment, the light-emitting layer has only 100% concentration of the organic molecules according to the invention, wherein the anode and cathode are applied to the substrate, and the light-emitting layer is applied between the anode and cathode.

[0279] In one specific embodiment of the organic optoelectronic device according to the present invention, a hole- and electron-injection layer has been applied between the anode and the cathode, while a hole- and electron-transport layer is between the hole- and electron-injection layer, and a light-emitting layer is between the hole- and electron-transport layer.

[0280] In a further specific embodiment of the present invention, the organic optoelectronic device comprises: a substrate, an anode, a cathode, and at least one hole-injection layer and one electron-transport layer, and at least one light-emitting layer, comprising an organic molecule according to the present invention and one or more host materials, wherein the triplet (T1) and singlet (S1) energy levels of the host material are located at higher energies than the triplet (T1) and singlet (S1) energy levels of the organic molecule, wherein the anode and cathode are applied to the substrate, and the hole-injection layer is applied between the anode and cathode, and the hole-transport layer is applied between the hole-injection layer and the electron-transport layer, and the light-emitting layer is applied between the hole-injection layer and the electron-transport layer.

[0281] In a further aspect, the present invention relates to a method for manufacturing optoelectronic components. This is achieved using organic molecules according to the present invention.

[0282] In one specific embodiment, the manufacturing method comprises treating the organic molecules according to the invention by vacuum evaporation or by solution treatment.

[0283] The present invention also includes a method of manufacturing a photoelectric device according to the present invention, wherein at least one layer of the photoelectric device

[0284] - It is coated using the sublimation method.

[0285] - It is coated using the OVPD (Organic Vapor Phase Deposition) method.

[0286] - It is coated by sublimation of a carrier gas, and / or

[0287] - Manufactured by solution or by printing.

[0288] In the manufacturing process of the optoelectronic device according to the present invention, known methods are used. Generally, these layers are individually applied to a suitable substrate in a series of deposition processing steps. In vapor deposition, commonly used methods such as thermal evaporation, chemical vapor deposition (CVD), and physical vapor deposition (PVD) may be employed. For active-matrix OLED displays, deposition is performed on an AMOLED substrate.

[0289] Alternatively, these layers may be applied by a solution or dispersion in a suitable solvent. Illustrative suitable coating methods include spin coating, dip coating, and jet printing. Each layer may be manufactured according to the invention by the same coating method or by different coating methods in various cases.

[0290] Example

[0291] General methods

[0292] GM1:

[0293]

[0294] In a round-bottom flask equipped with a reflux condenser, E1 (1 equivalent) was suspended in glacial acetic acid. After adding A1 (1.1 equivalent), the mixture was stirred at 100°C for 3 hours. After cooling, the reaction solution was concentrated as much as possible using a rotary evaporator. The residue was absorbed into CH2Cl2 and washed twice with saturated Na2CO3. The combined organic phases were dried over MgSO4. The solvent was removed using a rotary evaporator. After drying under high vacuum, E2 was obtained as the product, which can usually be used without further purification. If necessary, product E2 can be further purified by recrystallization.

[0295] The combination of illustrative A1 and E2

[0296]

[0297]

[0298]

[0299]

[0300] GM2:

[0301]

[0302] Initially, phthalimide E2 (1 equivalent), carbazole derivative E3 (1 equivalent), and K3PO4 (2 equivalents) were charged into a round-bottom flask and evacuated for 5 min. Under an inert atmosphere, anhydrous DMSO was added, and the reaction solution was stirred at 100 °C for 16 h. After cooling, the reaction solution was poured onto water and then extracted with CH2Cl2. After a second extraction with CH2Cl2, the combined organic phases were washed twice with water and saturated NaCl solution. The mixture was then dried over MgSO4, and the solvent was removed using a rotary evaporator. The products were purified by recrystallization.

[0303] GM3:

[0304]

[0305] n = 1 to 4, m = 0 to 4

[0306] Initially, E2 (1.2 equivalents), brominated carbazole E4 (1.0 equivalent), and K3PO4 (2 equivalents) were charged into a round-bottom flask, and the mixture was evacuated for 5 min. Under an inert atmosphere, anhydrous DMSO was added, and the reaction solution was stirred at 100 °C for 16 h. After cooling, the reaction solution was poured onto water and then extracted with CH2Cl2. After a second extraction with CH2Cl2, the combined organic phases were washed twice with water and saturated NaCl solution. The mixture was then dried over MgSO4, and the solvent was removed using a rotary evaporator. The products were purified by recrystallization.

[0307] According to the present invention, carbazole substituted with chlorine or iodine may also be used instead of carbazole substituted with bromine.

[0308] The combination of explanatory E4 and E5

[0309]

[0310]

[0311] GM4:

[0312] Phase 1

[0313]

[0314] Under nitrogen atmosphere, E5 (1.00 equivalent), bis(pinacolato)diboron (1.5 × (n + m) equivalent), tris(dibenzylacetone)dipalladium (0.01 equivalent), 2-(dicyclohexylphosphino)-2',4',6'-triisopropylbiphenyl (0.04 equivalent), and tripotassium phosphate (3n + 3m equivalent) were stirred in dioxane at 110 °C for 12 to 24 h. The resulting crude product could be purified by recrystallization.

[0315] Phase 2:

[0316]

[0317] Under nitrogen atmosphere, E6 (1.00 equivalent) and R b -Cl (1.3n + 1.3m equivalents), tris(dibenzylacetone)dipalladium (0.01 equivalents), 2-(dicyclohexylphosphino)-2',4',6'-triisopropylbiphenyl (0.04 equivalents), and tripotassium phosphate (2.5n + 2.5m equivalents) were stirred in a toluene / water (10:1) mixture at 100 °C for 12–24 h. The crude product was purified by rapid chromatography or by recrystallization.

[0318] R may also be used according to the present invention. b -Br or R b -I, not R b -Cl.

[0319] GM5:

[0320]

[0321] Under nitrogen atmosphere, E5 (1.00 equivalent) and appropriate R b Boric acid E7 (1.3n + 1.3m equivalents), tris(dibenzylacetone)dipalladium (0.01 equivalents), 2-(dicyclohexylphosphino)-2',4',6'-triisopropylbiphenyl (0.04 equivalents), and tripotassium phosphate (3n + 3m equivalents) were stirred in dioxane at 110 °C for 12–24 h. The crude product was purified by rapid chromatography or by recrystallization.

[0322] According to the present invention, the corresponding borate ester may also be used instead of boric acid.

[0323] The molecules according to the invention can each be obtained from GM2 or by combining GM3 and GM4 or GM3 and GM5. The products from these synthetic routes differ only in yield or purity obtained before purification. After appropriate purification, the products have equivalent quality.

[0324] Calculated using density functional theory

[0325] For the optimization of molecular structure, the BP86 functional was used (Becke, AD Phys. Rev. A 1988, 38, 3098-3100; Perdew, JP Phys. Rev. B 1986, 33, 8822-8827), and the identity analytical (RI) approximation was used (Sierka, M.; Hogekamp, ​​A.; Ahlrichs, RJ Chem. Phys. 2003, 118, 9136-9148; Becke, AD, J. Chem. Phys. 98 (1993) 5648-5652; Lee, C; Yang, W; Parr, RG Phys. Rev. B 37 (1988) 785-789). The excitation energies in the BP86-optimized structure were calculated using the B3LYP functional by the time-dependent DFT method (TD-DFT) (Becke, AD, J. Chem. Phys. 98 (1993) 5648-5652; Lee, C; Yang, W; Parr, RG Phys. Rev. B 37 (1988) 785-789; Vosko, SH; Wilk, L.; Nusair, M. Can. J. Phys. 58 (1980) 1200-1211; Stephens, PJ; Devlin, FJ; Chabalowski, CF; Frisch, MJJP Phys. Chem. 98 (1994) 11623-11627). Numerical integration was performed in all calculations using the def2-SV(P) basis set (Weigend, F.; Ahlrichs, R. Phys. Chem. Chem. Phys. 2005, 7, 3297-3305; Rappoport, D.; Furche, FJ Chem. Phys. 2010, 133, 134105 / 1-134105 / 11) and an m4 grid. All DFT calculations were performed using the Turbomole suite software (version 6.5) (TURBOMOLE V6.4 2012, developed by the University of Karlsruhe and Forschungszentrum Karlsruhe GmbH, 1989-2007, TURBOMOLE GmbH, since 2007; http: / / www.turbomole.com).

[0326] Optical physical measurement

[0327] Pretreatment of optical glass

[0328] After each use, clean all glassware (cuvettes and substrates made of quartz glass, diameter: 1 cm): rinse three times, each time using dichloromethane, acetone, ethanol, and deionized water, and place in a 5% Hellmanex solution for 24 hours, then rinse thoroughly with deionized water. To dry, blow the optical glassware dry with nitrogen gas.

[0329] Sample preparation: solution

[0330] Dissolve 1-2 mg of sample in 100 ml of a specific solvent; concentration 10 -5 mol / L. Seal the cuvette airtight and degas for 10 min.

[0331] Sample preparation, membrane: spin coating (instrument: Spin150, SPS euro).

[0332] The sample concentration is equivalent to 10 mg / ml, and it is composed of toluene or chlorobenzene.

[0333] Program: 1) 3 s at 400 rpm; 2) 20 sec at 1000 rpm; 3) 10 s at 4000 rpm. After coating, the film was dried in air at 70°C on an LHG precision heating plate for 1 min.

[0334] Absorption spectroscopy

[0335] Solution: Record the UV-vis spectrum on a Thermo Scientific instrument, model: Evolution 201. (See Sample Preparation: Solution)

[0336] Membrane: UV-vis spectra recorded on a Thermo Scientific Evolution 201 instrument. (See Sample Preparation, Membrane: Spin-coated)

[0337] Photoluminescence spectroscopy and TCSPC

[0338] Steady-state emission spectroscopy was performed using a Horiba Scientific FluoroMax-4 fluorescence spectrometer, equipped with a 150 W xenon arc lamp, excitation and emission monochromators, a Hamamatsu R928 photomultiplier tube, and a TSCPC option. Emission and excitation spectra were calibrated using standard calibration curves.

[0339] Emission decay time was also measured using this system, employing the TCSPC method with FM-2013 accessories and the TCSPC hub from Horiba YvonJobin. Excitation sources: NanoLED 370 (wavelength: 371 nm, pulse duration: 1.1 ns), NanoLED 290 (wavelength: 294 nm, pulse duration: <1 ns), SpectraLED 310 (wavelength: 314 nm), SpectraLED 355 (wavelength: 355 nm).

[0340] Evaluation (exponential fitting) was performed using the DataStation suite software and DAS 6 evaluation software. The fitting coefficients were described using the chi-square method.

[0341]

[0342] Where e i : Parameters predicted by the fitted model, and o i : The parameters that are measured.

[0343] Measurement of quantum efficiency

[0344] Photoluminescent quantum yield (PLQY) was measured using the Hamamatsu Photonics Absolute PLQuantum Yield Measurement C9920-03G system. This system consists of a 150W xenon discharge lamp, an automatically adjustable Czerny-Turner monochromator (250 nm to 950 nm), and an Ulbricht integrating sphere with a highly reflective Spectralon coating (a Teflon derivative), connected via fiber optic cable to a PMA-12 multichannel detector with a 1024 × 122 pixel BT (thin back-illuminated) CCD wafer (24 × 24 µm). Quantum efficiency and CIE coordinates were evaluated using U6039-05 software, version 3.6.0, for the G9920-OXG (PMA-12). Maximum emission is expressed in nm, quantum yield Φ in % (%), and CIE color coordinates as x and y values.

[0345] The following methods are used to determine the PLQY of polymer film, solution, and powder samples:

[0346] 1) Quality assurance implementation: The reference material used is anthracene in ethanol with a known concentration.

[0347] 2) Determination of excitation wavelength: First, determine the maximum absorption value of organic molecules and use it for excitation.

[0348] 3) Sample analysis: The absolute quantum yields of the degassed solution and membrane were determined under a nitrogen atmosphere. Calculations were performed within the system based on the following equations:

[0349]

[0350] Wherein, the number of photons n 光子 , and strength Int.

[0351] From the gas phase manufacturing and characterization of organic electroluminescent devices

[0352] The organic molecules of this invention may be used to produce OLED devices via vacuum sublimation. If a layer contains two or more components, their ratio is described as a mass percentage.

[0353] These currently unoptimized OLEDs can be characterized in a standard manner; for this purpose, the electroluminescence spectrum, the external quantum efficiency (measured as a percentage) as a function of brightness, which is calculated from the light and current detected by the photodiode, are recorded. The lifetime of the OLEDs can be determined from a graph of the electroluminescence spectrum versus time. The recorded LT50 value here corresponds to the time when the luminance has decreased to 50% of its initial value. Similarly, the LT70 value corresponds to the time when the luminance has decreased to 70% of its initial value.

[0354] Example 1

[0355]

[0356] Example 1 was prepared from 3-trifluoromethyl-9H-carbazole and N-trimethyl-3-fluorophthalimide according to GM2, with a yield of 49%.

[0357] 1 H NMR (500 MHz, chloroform-d) δ 8.40 (m, 1H), 8.17 (dt, J = 7.7, 1.0 Hz, 1H), 8.15 (dd, J = 7.4, 1.0 Hz, 1H), 8.05 (t, J = 7.7 Hz, 1H), 7.97 (dd, J =8.0, 1.0 Hz, 1H), 7.63 (dd, J = 8.8, 1.8 Hz, 1H), 7.46 (ddd, J = 8.3, 7.2,1.2 Hz, 1H), 7.37 (ddd, J = 8.0, 7.3, 1.0 Hz, 1H), 7.28 - 7.24 (m, 3H), 6.95-6.92 (m, 2H), 2.27 (s, 3H), 2.11 (s, 3H), 2.09 (s, 3H).

[0358] 19 F NMR (471 MHz, CDCl3) δ -60.38.

[0359] Figure 1 The emission spectrum of Example 1 (10% in PMMA) is shown. The emission maximum is at 469 nm. The photoluminescence quantum yield (PLQY) is 39%, and the full width at half maximum (FWHM) is 90 nm (0.49 eV). CIE was found. y The efficiency is 0.24 and the BMI is 163. The launch lifetime is 7.5 µs.

[0360] Example 2

[0361]

[0362] Example 2 was prepared from 3-trifluoromethyl-9H-carbazole and N-methyl-3-fluorophthalimide according to GM2, with a yield of 67%.

[0363] Figure 2 The emission spectrum of Example 2 (10% in PMMA) is shown. The emission maximum is at 458 nm. The photoluminescence quantum yield (PLQY) is 34%, and the full width at half maximum (FWHM) is 88 nm (0.50 eV). CIE was found. y The efficiency is 0.19 and the BMI is 179. The launch lifetime is 10.5 µs.

[0364] Example 3

[0365]

[0366] Example 3 was prepared from 2-trifluoromethyl-9H-carbazole and N-trimethyl-3-fluorophthalimide according to GM2, with a yield of 57%.

[0367] 1H NMR (500 MHz, chloroform-d) δ 8.22 (d, J = 8.1 Hz, 1H), 8.18 (dt, J =7.8, 0.9 Hz, 1H), 8.15 (dd, J = 7.4, 1.0 Hz, 1H), 8.06 (t, J = 7.8 Hz, 1H), 7.97 (dd, J = 8.0, 0.9 Hz, 1H), 7.56 (dd, J = 8.2, 1.4 Hz, 1H), 7.48 (ddd, J= 8.3, 7.2, 1.2 Hz, 1H), 7.44 (s, 1H), 7.37 (td, J = 7.6, 0.9 Hz, 1H), 7.31(d, J = 8.3 Hz, 1H), 6.95 (s, 1H), 6.93 (s, 1H), 2.27 (s, 3H), 2.12 (s, 3H), 2.09 (s, 3H).

[0368] Figure 3 The emission spectrum of Example 3 (10% in PMMA) is shown. The emission maximum is at 467 nm. The photoluminescence quantum yield (PLQY) is 46%, and the full width at half maximum (FWHM) is 86 nm (0.47 eV). CIE was found. y The efficiency is 0.22 and the BMI is 209. The launch lifetime is 8.5 µs.

[0369] Example 4

[0370]

[0371] Example 4 was prepared from 3-(3,6-dibromocarbazolyl)-N-methylphthalimide and 2,4-trifluoromethylphenyl-1-boronic acid according to GM5, with a yield of 44%.

[0372] 1 H NMR (500 MHz, chloroform-d) δ 8.09 (m, 2H), 8.06 (dd, J = 7.2, 1.2 Hz,1H), 8.05 - 8.03 (m, 2H), 7.99 (t, J = 7.6 Hz, 1H), 7.95 (dd, J = 8.0, 1.2Hz, 1H), 7.88 - 7.83 (m, 2H), 7.63 (d, J = 7.9 Hz, 2H), 7.39 (dd, J = 8.4,1.6 Hz, 2H), 7.23 (d, J = 8.4 Hz, 2H), 3.16 (s, 3H).

[0373] 19 F NMR (471 MHz, CDCl3) δ -57.00, -62.66.

[0374] Figure 4 The emission spectrum of Example 4 (10% in PMMA) is shown. The maximum emission is at 465 nm. The photoluminescence quantum yield (PLQY) is 50%, and the full width at half maximum (FWHM) is 89 nm (0.49 eV). CIE was found. y The value is 0.21 and the BMI is 238.

[0375] Example 5

[0376]

[0377] Example 5 was prepared from 3-cyano-9H-carbazole and N-trimethyl-3-fluorophthalimide according to GM2, with a yield of 62%.

[0378] 1 ¹H NMR (500 MHz, chloroform-d) δ 8.47 - 8.43 (m, 1H), 8.18-8.14 (m, 2H), 8.07 (t, J = 7.7 Hz, 1H), 7.96 (dd, J = 8.0, 1.0 Hz, 1H), 7.64 (dd, J = 8.5, 1.6 Hz, 1H), 7.49 (ddd, J = 8.4, 7.3, 1.2 Hz, 1H), 7.42-7.37 (m, 1H), 7.28-7.22 (m, 2H), 6.93 (m, 2H), 2.27 (s, 3H), 2.10 (s, 3H), 2.07 (s, 3H).

[0379] Figure 5 The emission spectrum of Example 5 (10% in PMMA) is shown. The maximum emission is at 462 nm. The photoluminescence quantum yield (PLQY) is 36%, and the full width at half maximum (FWHM) is 87 nm (0.49 eV). CIE was found. y The value is 0.20 and the BMI is 180. The launch lifetime is 6.6 µs.

[0380] Example 6

[0381]

[0382] Example 6 was prepared from 3-(3,6-dibromocarbazolyl)-N-methylphthalimide and 2-cyanobenzoboronic acid according to GM5, with a yield of 61%.

[0383] 1 H NMR (500 MHz, chloroform-d) δ 8.38 (d, J = 1.7 Hz, 2H), 8.06 (dd, J =7.3, 1.1 Hz, 1H), 7.99 (t, J = 7.7 Hz, 1H), 7.93 (dd, J = 7.9, 1.1 Hz, 1H), 7.83 - 7.78 (m, 2H), 7.71 - 7.63 (m, 6H), 7.45 (ddd, J = 7.8, 6.4, 2.3 Hz, 2H), 7.28 (d, J = 8.5 Hz, 2H), 3.15 (d, J = 1.1 Hz, 3H).

[0384] Figure 6 The emission spectrum of Example 6 (10% in PMMA) is shown. The emission maximum is at 477 nm. The photoluminescence quantum yield (PLQY) is 56%, and the full width at half maximum (FWHM) is 93 nm (0.48 eV). CIE was found. y The value is 0.30 and the BMI is 187. The launch lifetime is 59 µs.

[0385] Example 7

[0386]

[0387] Example 7 was prepared from 3-(3,6-dibromocarbazolyl)-N-trimethylmethylphthalimide and pyrimidine-5-boronic acid according to GM5, with a yield of 22%.

[0388] 1 H NMR (500 MHz, chloroform-d) δ 9.22 (s, 2H), 9.07 (s, 4H), 8.40 (d, J =1.7 Hz, 2H), 8.21-8.17 (m, 1H), 8.11 (t, J = 7.7 Hz, 1H), 8.06 - 8.01 (m,1H), 7.65 (dd, J = 8.5, 1.8 Hz, 2H), 7.39 (d, J = 8.5 Hz, 2H), 6.93 (s, 2H), 2.26 (s, 3H), 2.11 (s, 6H).

[0389] Figure 7The emission spectrum of Example 7 (10% in PMMA) is shown. The emission maximum is at 490 nm. The photoluminescence quantum yield (PLQY) is 58%, and the full width at half maximum (FWHM) is 97 nm (0.48 eV). CIE was found. y The efficiency is 0.38 and the BMI is 153. The launch lifetime is 9.8 µs.

[0390] Example 8

[0391]

[0392] Example 8 was prepared from N-trimethylmethyl-3-fluorophthalimide and 9H-pyrido[2,3-b]indole according to GM2, with a yield of 26%.

[0393] 1 H NMR (500 MHz, chloroform-d) δ 8.41 - 8.35 (m, 2H), 8.14-8.11 (m, 1H), 8.09 (dd, J = 6.4, 2.0 Hz, 1H), 8.06 - 8.00 (m, 2H), 7.47 (td, J = 7.6, 7.1,1.2 Hz, 1H), 7.38 - 7.33 (m, 2H), 7.25 (dd, J = 7.7, 4.9 Hz, 1H), 6.93 (s,1H), 6.91 (s, 1H), 2.26 (s, 3H), 2.14 (s, 3H), 2.08 (s, 3H).

[0394] Figure 8 The emission spectrum of Example 8 (10% in PMMA) is shown. The maximum emission is at 448 nm. The photoluminescence quantum yield (PLQY) is 32%, and the full width at half maximum (FWHM) is 86 nm (0.51 eV). CIE was found. y The value is 0.15 and the BMI is 213.

[0395] Example 9

[0396]

[0397] Example 9 was synthesized by the following method:

[0398] Under a nitrogen atmosphere, 3-(2-bromocarbazolyl)-N-trimethylmethylphthalimide (1 equivalent) and CuCN (1.5 equivalent) were heated to 150 °C for 24 h in anhydrous DMF (2 ml per mmol of aryl bromide). After cooling to room temperature, the resulting brown precipitate was filtered off and washed with DMF. The crude product, a yellow-green solid precipitate, was obtained by adding twice the volume of water to the filtrate. The precipitate was filtered off, washed with water, and reabsorbed in ethyl acetate. The resulting solution was dried over MgSO4 and the solvent was removed under reduced pressure. The residue was purified by MPLC (precipitate: CH2Cl2 / cyclohexane 50:50 - 100:0). Yield: 12%.

[0399] 1 H NMR (500 MHz, chloroform-d) δ 8.20 (dd, J = 8.0, 0.7 Hz, 1H), 8.19-8.15(m, 2H), 8.08 (t, J = 7.7 Hz, 1H), 7.97 (dd, J = 8.0, 1.0 Hz, 1H), 7.56 (dd,J = 8.1, 1.3 Hz, 1H), 7.53 - 7.47 (m, 2H), 7.38 (ddd, J = 8.0, 7.2, 0.9 Hz,1H), 7.30 - 7.27 (m, 1H), 6.95 (s, 1H), 6.93 (s, 1H), 2.28 (s, 3H), 2.14 (s,3H), 2.08 (s, 3H).

[0400] Figure 9 The emission spectrum of Example 9 (10% in PMMA) is shown. The maximum emission is at 463 nm. The photoluminescence quantum yield (PLQY) is 36%, and the full width at half maximum (FWHM) is 87 nm (0.48 eV). CIE was found. y The value is 0.21 and the BMI is 171.

[0401] Example 10

[0402]

[0403] Example 10 was prepared from 3-(3-bromocarbazolyl)-N-methylphthalimide and 2,4-bis(trifluoromethyl)phenylboronic acid according to GM5, with a yield of 46%.

[0404] 1H NMR (500 MHz, chloroform-d) δ 8.14 (dt, J = 7.7, 0.9 Hz, 1H), 8.10 (d, J= 1.6 Hz, 1H), 8.06 - 8.04 (m, 1H), 8.03 (dd, J = 7.3, 1.1 Hz, 1H), 7.98 -7.93 (m, 1H), 7.90 (dd, J = 8.0, 1.1 Hz, 1H), 7.88 - 7.84 (m, 1H), 7.63 (d, J= 8.0 Hz, 1H), 7.43 (ddd, J = 8.4, 7.2, 1.2 Hz, 1H), 7.37 - 7.31 (m, 2H),7.20 (d, J = 8.4 Hz, 1H), 7.18-7.16 (m, 1H), 3.14 (s, 3H).

[0405] 19 F NMR (471 MHz, CDCl3) δ -57.02, -62.64.

[0406] Figure 10 The emission spectrum of Example 10 (10% in PMMA) is shown. The maximum emission is at 474 nm. The photoluminescence quantum yield (PLQY) is 61%, and the full width at half maximum (FWHM) is 92 nm (0.49 eV). CIE was found. y The efficiency is 0.28 and the BMI is 218. The launch lifetime is 7.0 µs.

[0407] Example 11

[0408]

[0409] Example 11 was prepared from 3-(1-bromocarbazolyl)-N-trimethylmethylphthalimide and 4-cyanobenzonic acid according to GM5, with a yield of 22%.

[0410] 1H NMR (500 MHz, chloroform-d) δ 8.22 (dd, J = 7.8, 1.2 Hz, 1H), 8.19-8.16(m, 1H), 7.80 (dd, J = 7.4, 0.9 Hz, 1H), 7.56 (t, J = 7.7 Hz, 1H), 7.44 -7.37 (m, 3H), 7.37 - 7.24 (m, 7H), 7.05 (dt, J = 8.2, 0.9 Hz, 1H), 6.96 (s,1H), 6.90 (s, 1H), 2.27 (s, 3H), 2.15 (s, 3H), 1.99 (s, 3H).

[0411] Figure 11 The emission spectrum of Example 11 (10% in PMMA) is shown. The maximum emission is at 482 nm. The photoluminescence quantum yield (PLQY) is 61%, and the full width at half maximum (FWHM) is 94 nm (0.48 eV). CIE was found. y The value is 0.33 and the BMI is 185.

[0412] Example 12

[0413]

[0414] Example 12 was prepared by the following method:

[0415] Under a nitrogen atmosphere, 3-(1-bromocarbazolyl)-N-trimethylmethylphthalimide (1 equivalent) and CuCN (1.5 equivalent) were heated to 250 °C for at least 15 h in anhydrous DMF in a double-necked flask equipped with a reflux condenser. After cooling to RT, the crude product was precipitated from the reaction solution by adding an equal volume of water. The precipitate was filtered off and treated with CH2Cl2. The resulting solution was washed with water, dried over MgSO4, and the solvent was released under reduced pressure. The residue was washed with hot ethanol. The washing solution was discarded, and the residue was then recrystallized from toluene. Yield: 69%.

[0416] 1H NMR (500 MHz, chloroform-d): δ = 8.35 (dd, J = 7.9, 1.2 Hz, 1H), 8.19 (dd,J = 7.4, 1.0 Hz, 1H), 8.16 (dt, J = 7.8, 0.9 Hz, 1H), 8.05 (t, J = 7.7 Hz,1H), 7.98 (dd, J = 7.9, 0.9 Hz, 1H), 7.66 (dd, J = 7.6, 1.2 Hz, 1H), 7.48(ddd, J = 8.3, 7.2, 1.2 Hz, 1H), 7.39 (td, J = 7.6, 0.9 Hz, 1H), 7.33 (t, J =7.7 Hz, 1H), 7.24 (dt, J = 8.3, 0.8 Hz, 1H), 6.94 (bs, 1H), 6.87 (bs, 1H), 2.25 (s, 3H), 2.20 (s, 3H), 2.00 (s, 3H) ppm.

[0417] Figure 12 The emission spectrum of Example 12 (10% in PMMA) is shown. The maximum emission is at 453 nm. The photoluminescence quantum yield (PLQY) is 44%, and the full width at half maximum (FWHM) is 84 nm (0.49 eV). CIE was found. y The value is 0.16 and the BMI is 275.

[0418] Example 13

[0419]

[0420] Example 13 was prepared from 3-(3-bromocarbazolyl)-N-methylphthalimide according to GM4, with a yield of 57%.

[0421] 1H NMR (500 MHz, chloroform-d) δ 9.62-9.61 (m, 1H), 8.89 (dd, J = 8.7, 1.7Hz, 1H), 8.86 - 8.81 (m, 4H), 8.41-8.38 (m, 1H), 8.07 (dd, J = 7.3, 1.0 Hz,1H), 7.99 (t, J = 7.6 Hz, 1H), 7.93 (dd, J = 7.9, 1.0 Hz, 1H), 7.66 - 7.58(m, 6H), 7.48-7.44 (m, 1H), 7.42 (td, J = 7.4, 1.2 Hz, 1H), 7.29 - 7.26 (m,1H), 7.21 - 7.19 (m, 1H), 3.13 (s, 3H).

[0422] Figure 13 The emission spectrum of Example 13 (10% in PMMA) is shown. The maximum emission is at 478 nm. The photoluminescence quantum yield (PLQY) is 58%, and the full width at half maximum (FWHM) is 92 nm (0.48 eV). CIE was found. y The value is 0.30 and the BMI is 193.

[0423] Example 14

[0424]

[0425] Example 14 was prepared from 3-(1-bromocarbazolyl)-N-trimethylmethylphthalimide and 3,5-bis(trifluoromethyl)phenylboronic acid according to GM5, with a yield of 49%.

[0426] 1H NMR (500 MHz, chloroform-d) δ 8.26 (dd, J = 7.8, 1.2 Hz, 1H), 8.20 - 8.16(m, 1H), 7.76 (dd, J = 7.4, 0.9 Hz, 1H), 7.79 - 7.47 (br. s., 2H), 7.61 (s,1H), 7.45 (t, J = 7.6 Hz, 1H), 7.41 (t, J =7.41 Hz, 1H), 7.39 - 7.32 (m, 3H), 7.25 (dd, J = 8.0, 0.9 Hz, 1H), 7.01 - 6.97 (m, 1H), 6.95 - 6.92 (m, 1H), 6.91-6.89 (m, 1H), 2.27 (s, 3H), 2.10 (s, 3H), 2.03 (s, 3H).

[0427] 19 F NMR (471 MHz, CDCl3) δ -62.5.

[0428] Figure 14 The emission spectrum of Example 14 (10% in PMMA) is shown. The emission maximum is at 477 nm. The photoluminescence quantum yield (PLQY) is 65%, and the full width at half maximum (FWHM) is 93 nm (0.48 eV). CIE was found. y The value is 0.31 and the BMI is 210.

[0429] Example 15

[0430]

[0431] 1H NMR (500 MHz, chloroform-d) δ 8.65 (dd, J = 1.7, 0.6 Hz, 1H), 8.17 (dt, J= 7.8, 1.0 Hz, 1H), 8.06 (dd, J = 7.4, 1.0 Hz, 1H), 7.98 (t, J = 7.8 Hz, 1H), 7.96 (dd, J = 8.6, 1.6 Hz, 1H), 7.89-7.85 (m, 3H), 7.64 - 7.59 (m, 1H), 7.55-7.50 (m, 2H), 7.44 (ddd, J = 8.3, 7.2, 1.2 Hz, 1H), 7.36 (ddd, J = 8.1, 7.2,1.0 Hz, 1H), 7.19 - 7.15 (m, 2H), 3.12 (s, 3H).

[0432] Figure 15 The emission spectrum of Example 15 (10% in PMMA) is shown. The emission maximum is at 467 nm. The photoluminescence quantum yield (PLQY) is 48%, and the full width at half maximum (FWHM) is 92 nm (0.50 eV). CIE was found. y The value is 0.24 and the BMI is 200.

[0433] Example 16

[0434]

[0435] Example 16 was prepared according to GM4 by converting 3-(3-bromocarbazolyl)-N-ylphthalimide to the corresponding pinacol ester of borate and then reacting it with N-trimethyl-3-chlorophthalimide, with a yield of 87%.

[0436] 1H NMR (500 MHz, chloroform-d) δ 8.14 (d, J = 7.7 Hz, 1H), 8.10 (dd, J =6.9, 1.4 Hz, 1H), 8.03 - 7.99 (m, 1H), 7.99 - 7.94 (m, 2H), 7.89 - 7.82 (m,2H), 7.68 (dd, J = 8.5, 1.8 Hz, 1H), 7.40 (ddd, J = 8.3, 7.2, 1.2 Hz, 1H),7.35-7.23 (m, 4H), 6.97 (s, 2H), 6.93 (m, 2H), 2.30 (s, 3H), 2.27 (s, 3H),2.14 (s, 3H), 2.13 (s, 3H), 2.12 (s, 3H), 2.11 (s, 3H).

[0437] Figure 16 The emission spectrum of Example 16 (10% in PMMA) is shown. The maximum emission is at 489 nm. The photoluminescence quantum yield (PLQY) is 59%, and the full width at half maximum (FWHM) is 97 nm (0.48 eV). CIE was found. y The value was 0.39 and the BMI was 151.

[0438] Example 17

[0439]

[0440] Example 17 was prepared according to GM4 by converting 3-(3,6-dibromocarbazolyl)-N-trimethylmethylphthalimide to the corresponding bis(pinacol borate) ester and then reacting it with dichlorophenyltriazine, with a yield of 79%.

[0441] 1 H NMR (500 MHz, chloroform-d): δ = 9.77 (dd, J = 1.7, 0.6 Hz, 2H), 8.93 (dd,J = 8.7, 1.7 Hz, 2H), 8.88 - 8.86 (m, 8H), 8.23 ​​(dd, J = 7.2, 1.2 Hz, 1H), 8.15 - 8.09 (m, 2H), 7.68 - 7.62 (m, 12H), 7.40 (dd, J = 8.6, 0.6 Hz, 2H), 6.94 (s, 2H), 2.26 (s, 3H), 2.16 (s, 6H) ppm.

[0442] Figure 17 The emission spectrum of Example 17 (10% in PMMA) is shown. The maximum emission is at 488 nm. The photoluminescence quantum yield (PLQY) is 55%, and the full width at half maximum (FWHM) is 94 nm (0.47 eV). CIE was found. y The value was 0.37 and the BMI was 149.

[0443] Example 18

[0444]

[0445] Example 18 was prepared from 3-(4-bromocarbazolyl)-N-trimethylmethylphthalimide and 3,5-bis(trifluoromethyl)phenylboronic acid according to GM5, with a yield of 63%.

[0446] 1 H NMR (500 MHz, chloroform-d): δ = 8.16 (d, J = 1.0 Hz, 1H), 8.15 (d, J =1.0 Hz, 2H), 8.07 (t, J = 7.7 Hz, 1H), 8.01 (s, 1H), 7.99 (dd, J = 7.9, 1.0Hz, 1H), 7.46 (dd, J = 8.3, 7.3 Hz, 1H), 7.37 (ddd, J = 8.3, 7.1, 1.2 Hz, 1H), 7.33 (dt, J = 8.1, 0.9 Hz, 1H), 7.28 (dd, J = 8.3, 0.9 Hz, 1H), 7.24 (d,J = 8.1 Hz, 1H), 7.17 (dd, J = 7.4, 0.9 Hz, 1H), 7.08 (ddd, J = 8.1, 7.1, 1.0Hz, 1H), 6.93 (s, 2H), 2.27 (s, 3H), 2.12 (s, 3H), 2.09 (s, 3H) ppm.

[0447] Figure 18 The emission spectrum of Example 18 (10% in PMMA) is shown. The maximum emission is at 480 nm. The photoluminescence quantum yield (PLQY) is 58%, and the full width at half maximum (FWHM) is 92 nm (0.48 eV). CIE was found. y The value is 0.31 and the BMI is 187.

[0448] Example 19

[0449]

[0450] Example 19 was prepared from 3-(4-bromocarbazolyl)-N-trimethylmethylphthalimide and 4-cyanobenzoboronic acid according to GM5, with a yield of 42%.

[0451] 1 H NMR (500 MHz, chloroform-d): δ = 8.14 (dd, J = 7.4, 1.0 Hz, 1H), 8.05 (t,J = 7.7 Hz, 1H), 7.98 (dd, J = 8.0, 1.0 Hz, 1H), 7.85 - 7.76 (m, 2H), 7.78 -7.76 (m, 2H), 7.44 (dd, J = 8.3, 7.3 Hz, 1H), 7.40 (dt, J = 8.0, 0.9 Hz, 1H), 7.35 - 7.33 (m, 1H), 7.24 (d, 1H), 7.22 (dt, J = 8.3, 0.9 Hz, 1H), 7.12 (dd,J = 7.3, 0.9 Hz, 1H), 7.07 (ddd, J = 8.1, 7.0, 1.0 Hz, 1H), 6.93 (s, 2H), 2.27 (s, 3H), 2.12 (s, 3H), 2.09 (s, 3H) ppm.

[0452] Figure 19 The emission spectrum of Example 19 (10% in PMMA) is shown. The maximum emission is at 486 nm. The photoluminescence quantum yield (PLQY) is 56%, and the full width at half maximum (FWHM) is 94 nm (0.47 eV). CIE was found. y The value is 0.36 and the BMI is 156.

[0453] Example 20

[0454]

[0455] Example 20 was prepared from 3-(3,6-dibromocarbazolyl)-N-trimethylmethylphthalimide and 2-trifluoromethylphenylboronic acid according to GM5, with a yield of 40%.

[0456] 1H NMR (500 MHz, chloroform-d): δ = 8.12 (dd, J = 7.1, 1.3 Hz, 1H), 8.09 -8.03 (m, 4H), 7.77 (d, J = 7.7 Hz, 2H), 7.58 (t, J = 7.6 Hz, 2H), 7.48 (d, J= 7.9 Hz, 2H), 7.44 (d, J = 7.8 Hz, 2H), 7.38 (d, J = 7.4 Hz, 2H), 7.28 (d, J= 8.5 Hz, 2H), 6.96 (s, 2H), 2.29 (s, 3H), 2.14 (s, 6H) ppm.

[0457] The emission spectrum of Example 20 (10% in PMMA) was measured. The maximum emission was at 484 nm. The photoluminescence quantum yield (PLQY) was 68%, and the full width at half maximum (FWHM) was 94 nm (0.48 eV). CIE was found. y The value is 0.35 and the BMI is 194.

[0458] Example 21

[0459]

[0460] Example 21 was prepared from 3-(3-bromocarbazolyl)-N-(o-phenyl)phthalimide according to GM4, with a yield of 66%.

[0461] 1 ¹H NMR (500 MHz, chloroform-d): δ (ppm) = 9.54 (dd, J = 12.2, 1.6 Hz), 8.87–8.85 (m), 8.83–8.81 (m), 8.73 (dd, J = 8.7, 1.7 Hz), 8.33–8.31 (m), 8.05 (td, J = 7.5, 1.0 Hz), 7.98 (td, J = 7.7, 3.1 Hz, 1H), 7.92 (dd, J = 7.9, 1.1 Hz), 7.91 (dd, J = 7.9, 1.1 Hz), 7.65–7.27 (m), 6.60–6.57 (m). The product consists of two rotational isomers, whose NMR signals are mutually obfuscated.

[0462] Figure 21The emission spectrum of Example 21 (10% in PMMA) is shown. The maximum emission is at 481 nm. The photoluminescence quantum yield (PLQY) is 68%, and the full width at half maximum (FWHM) is 92 nm (0.47 eV). CIE was found. y The efficiency is 0.33 and the BMI is 206. The launch lifetime is 5.7 µs.

[0463] Example 22

[0464]

[0465] Example 22 was prepared from 3-(3-bromocarbazolyl)-N-(o-phenyl)phthalimide according to GM4, with a yield of 42%.

[0466] The emission spectrum of Example 22 (10% in PMMA) was recorded. The maximum emission was at 489 nm. The photoluminescence quantum yield (PLQY) was 62%, and the full width at half maximum (FWHM) was 97 nm (0.48 eV). CIE was found. y The efficiency is 0.37 and the BMI is 168. The launch lifetime is 5.9 µs.

[0467] Example 23

[0468]

[0469] Example 23 was prepared from 3-(3,6-dibromocarbazolyl)-N-(o-phenyl)phthalimide and 2-trifluoromethylphenylboronic acid according to GM5, with a yield of 80%.

[0470] The emission spectrum of Example 23 (10% in PMMA) was measured. The emission maximum was at 483 nm. The photoluminescence quantum yield (PLQY) was 68%, and the full width at half maximum (FWHM) was 93 nm (0.47 eV). CIE was found. y The value is 0.34 and the BMI is 200.

[0471] Example 24

[0472]

[0473] Example 24 was prepared according to GM4 by converting 3-(3-bromocarbazolyl)-N-(o-phenyl)phthalimide to the corresponding bis(pinacol borate) ester and then reacting it with 3-bromo-6-trifluoromethylbenzyl nitrile, in a yield of 64%.

[0474] The emission spectrum of Example 24 (10% in PMMA) was measured. The maximum emission value was 491 nm. The photoluminescence quantum yield (PLQY) was 65%, and the full width at half maximum (FWHM) was 96 nm (0.48 eV). CIE was found... y The value is 0.37 and the BMI is 176.

[0475] Example 25

[0476]

[0477] Example 25 was prepared according to GM4 by converting 3-(2-bromocarbazolyl)-N-(o-biphenyl)phthalimide to the corresponding bis(pinacol borate) ester and then reacting it with 2-bromobenzyl nitrile, in a yield of 97%.

[0478] The emission spectrum of Example 25 (10% in PMMA) was recorded. The maximum emission was at 476 nm. The photoluminescence quantum yield (PLQY) was 61%, and the full width at half maximum (FWHM) was 91 nm (0.48 eV). CIE was found. y The value is 0.29 and the BMI is 210.

[0479] Example 26

[0480]

[0481] Example 26 was prepared according to GM4 by converting 3-(2-bromocarbazolyl)-N-(o-(meta-triphenyl))phthalimide to the corresponding bis(pinacol borate) ester and then reacting it with dichlorophenyltriazine, in a yield of 44%.

[0482] The emission spectrum of Example 26 (10% in PMMA) was recorded. The maximum emission was at 486 nm. The photoluminescence quantum yield (PLQY) was 65%, and the full width at half maximum (FWHM) was 93 nm (0.47 eV). CIE was found. y The value is 0.36 and the BMI is 181. The launch lifetime is 5.6 µs.

[0483] Example 27

[0484]

[0485] Example 27 was prepared according to GM4 by converting 3-(2-bromocarbazolyl)-N-(o-biphenyl)phthalimide to the corresponding bis(pinacol borate) ester and then reacting it with 2-bromo-6-cyanopyridine in 13% yield.

[0486] The emission spectrum of Example 27 (10% in PMMA) was recorded. The maximum emission was at 489 nm. The photoluminescence quantum yield (PLQY) was 61%, and the full width at half maximum (FWHM) was 97 nm (0.48 eV). CIE was found. y The value is 0.38 and the BMI is 160.

[0487] Example 28

[0488]

[0489] Example 28 was prepared according to GM4 by converting 3-(3-bromocarbazolyl)-N-(o-phenyl)phthalimide to the corresponding bis(pinacol borate) ester and then reacting it with 4-bromo-3-trifluoromethylbenzyl nitrile, in a yield of 94%.

[0490] The emission spectrum of Example 28 (10% in PMMA) was measured. The maximum emission was at 479 nm. The photoluminescence quantum yield (PLQY) was 63%, and the full width at half maximum (FWHM) was 92 nm (0.46 eV). CIE was found... y The value is 0.31 and the BMI is 203.

[0491] Example 29

[0492]

[0493] Example 29 was prepared according to GM4 by converting 3-(3-bromocarbazolyl)-N-(o-phenyl)phthalimide to the corresponding bis(pinacol borate) ester and then reacting it with 2-bromo-5-trifluoromethylbenzyl nitrile, in a yield of 36%.

[0494] The emission spectrum of Example 29 (10% in PMMA) was measured. The maximum emission value was 475 nm. The photoluminescence quantum yield (PLQY) was 67%, and the full width at half maximum (FWHM) was 91 nm (0.48 eV). CIE was found... y The value is 0.29 and the BMI is 231.

[0495] Example 30

[0496]

[0497] Example 30 was prepared according to GM4 by converting 3-(3-bromocarbazolyl)-N-(o-phenyl)phthalimide to the corresponding borate pinacol ester and then reacting it with N-(o-phenyl)phthalimide-3-chlorophthalimide, in a yield of 45%.

[0498] The emission spectrum of Example 30 (10% in PMMA) was measured. The maximum emission was at 490 nm. The photoluminescence quantum yield (PLQY) was 61%, and the full width at half maximum (FWHM) was 96 nm (0.48 eV). CIE was found. y The value is 0.38 and the BMI is 161.

[0499] Example 31

[0500]

[0501] Example 31 was prepared according to GM4 by converting 3-(4-bromocarbazolyl)-N-(o-phenyl)phthalimide to the corresponding bis(pinacol borate) ester and then reacting it with 3-bromo-6-trifluoromethylbenzyl nitrile in a yield of 40%.

[0502] The emission spectrum of Example 31 (10% in PMMA) was measured. The maximum emission was at 474 nm. The photoluminescence quantum yield (PLQY) was 61%, and the full width at half maximum (FWHM) was 93 nm (0.48 eV). CIE was found. y The value is 0.33 and the BMI is 203.

[0503] Example 32

[0504]

[0505] Example 32 was prepared from 3-(2-bromocarbazolyl)-N-(o-phenyl)phthalimide and 3-cyanobenzoic acid according to GM5, with a yield of 31%.

[0506] The emission spectrum of Example 32 (10% in PMMA) was measured. The maximum emission was at 474 nm. The photoluminescence quantum yield (PLQY) was 54%, and the full width at half maximum (FWHM) was 93 nm (0.48 eV). CIE was found. y The value is 0.32 and the BMI is 169.

[0507] Examples D1 and D2:

[0508] Examples 3 and 5 were tested in OLEDs having the following structures:

[0509]

[0510]

[0511] Performance data

[0512]

[0513] Example D3

[0514] Example 21 was tested in an OLED module (“Module D3”) having the following structure (the proportion of molecules in the emitter layer according to the present invention is expressed as a mass percentage):

[0515]

[0516] Performance data

[0517]

[0518] The maximum emission wavelength is 478 nm.

[0519]

[0520] Example D4

[0521] Example 21 was tested in an OLED module ("Module D4") having the following structure (the proportion of molecules in the emitter layer according to the present invention is expressed as a mass percentage):

[0522]

[0523] Performance data

[0524]

[0525] The maximum emission value is at 486 nm; at 4.5 V, CIEx is determined to be 0.24 and CIEy to be 0.39.

[0526] Further examples:

[0527]

[0528]

[0529]

[0530]

[0531]

[0532]

[0533]

[0534]

[0535]

[0536]

[0537]

[0538]

[0539]

[0540]

[0541]

[0542]

[0543]

[0544]

[0545]

[0546]

[0547]

[0548]

[0549]

[0550]

[0551]

[0552]

[0553]

[0554]

[0555]

[0556]

[0557]

[0558]

[0559]

[0560]

[0561]

[0562]

[0563]

[0564]

[0565]

[0566]

[0567]

[0568]

[0569]

[0570]

[0571]

[0572]

[0573]

[0574]

[0575]

[0576]

[0577]

[0578]

[0579]

[0580]

[0581]

[0582]

[0583]

[0584]

[0585]

[0586]

[0587] 。

[0588] Attached Figure

[0589] The attached image shows:

[0590] Figure 1 Emission spectrum of 1 (10% in PMMA).

[0591] Figure 2 Emission spectrum of 2 (10% in PMMA).

[0592] Figure 3 Emission spectrum of 3 (10% in PMMA).

[0593] Figure 4 4 (10% in PMMA) emission spectrum.

[0594] Figure 5 Emission spectrum of 5 (10% in PMMA).

[0595] Figure 6 Emission spectrum of 6 (10% in PMMA).

[0596] Figure 7 Emission spectrum of 7 (10% in PMMA).

[0597] Figure 8 Emission spectrum of 8 (10% in PMMA).

[0598] Figure 9 Emission spectrum of 9 (10% in PMMA).

[0599] Figure 10 Emission spectrum of 10 (10% in PMMA).

[0600] Figure 11 Emission spectrum of 11 (10% in PMMA).

[0601] Figure 12 Emission spectrum of 12 (10% in PMMA).

[0602] Figure 13 Emission spectrum of 13 (10% in PMMA).

[0603] Figure 14 Emission spectrum of 14 (10% in PMMA).

[0604] Figure 15 Emission spectrum of 15 (10% in PMMA).

[0605] Figure 16 Emission spectrum of 16 (10% in PMMA).

[0606] Figure 17 Emission spectrum of 17 (10% in PMMA).

[0607] Figure 18 Emission spectrum of 18 (10% in PMMA).

[0608] Figure 19 Emission spectrum of 19 (10% in PMMA).

[0609] Figure 20 Emission spectrum of 20 (10% in PMMA).

[0610] Figure 21 Emission spectrum of 21 (10% in PMMA).

Claims

1. An organic molecule with the structure of formula A2, A5, A6, or A7. or in, R N It is trimethylbenzyl, biphenyl, or triphenyl; R a and R d H is independent in each case; R c The group that is independently of formula T1 in each case: in, R N2 For those that have not been replaced or have been replaced by one or more R N3 Substituted phenyl; R N3 It is methyl or phenyl; And in this context, # indicates the position where the group of formula T1 is connected by a single bond.

2. The organic molecule according to claim 1, wherein, The molecule has at least one CN group.

3. Use of an organic molecule according to claim 1 or 2, as an emitter and / or host.

4. A composition comprising or consisting of the following components: (a) at least one organic molecule according to claim 1 or 2, particularly as an emitter and / or host, and (b) One or more emitters and / or host materials other than the molecules according to claim 1 or 2, and (c) One or more dyes and / or one or more solvents may be selected.

5. An optoelectronic component comprising the organic molecule according to claim 1 or 2 or the composition according to claim 4.

6. The optoelectronic component according to claim 5, comprising: -Substrate, - Anode and - Cathode, wherein the anode or cathode has been applied to the substrate, and - At least one light-emitting layer disposed between the anode and the cathode and containing the organic molecule according to claim 1 or 2 or the composition according to claim 4.

7. A method for manufacturing an optoelectronic component, wherein, The organic molecule described in claim 1 or 2 was used.

8. The method according to claim 7, wherein, The organic molecule is applied through an evaporation process or by a solution.

Images