ORGANIC COMPOUND AND ORGANIC ELECTROLUMINESCENCE DEVICE USING THE SAME

Abstract

An organic compound is described. An organic electroluminescence device comprises the organic compound, as a host of an emissive layer, or as a hole blocking layer. The organic compound may increase a half-life or current efficiency of the organic electroluminescence device. The organic compound may lower a driving voltage of the organic electroluminescence device. The mentioned organic compound may have the following formula:

##STR00001##

The same definition as described in the present invention.

Claims

1. An organic compound having the formula as follows: ##STR00138## wherein P is a divalent bridge selected from the group consisting of NAr, O, S, CR.sub.5R.sub.6 and SiR.sub.7R.sub.8; Q is a single bond or a divalent bridge selected from the group consisting of NAr, O, S, CR.sub.5R.sub.6 and SiR.sub.7R.sub.8; at least one of X and Y is NAr; X is a divalent bridge selected from the group consisting of O, S, CR.sub.5R.sub.6 and SiR.sub.7R.sub.8 if X is not NAr; Y is a divalent bridge selected from the group consisting of O, S, CR.sub.5R.sub.6 and SiR.sub.7R.sub.8 if Y is not NAr; A represents a substituted or unsubstituted fused ring hydrocarbons unit having two rings; H represents a substituted or unsubstituted fused ring hydrocarbons unit having one or two rings; Ar represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; and R.sub.1 to R.sub.8 are independently selected from the group consisting of a hydrogen atom, a halide, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms; a substituted or unsubstituted arylamine group having 6 to 30 ring carbon atoms, and a substituted or unsubstituted heteroarylamine group having 5 to 30 ring carbon atoms.

2. The organic compound according to claim 1, wherein the organic compound has one of the following formula (3) to formula (26): ##STR00139## ##STR00140## ##STR00141## ##STR00142## ##STR00143## ##STR00144##

3. The organic compound according to claim 1, wherein the alkyl group, aralkyl group, aryl group, heteroaryl group, arylamine group, or heteroarylamine group is substituted by a halogen, an alkyl group, an aryl group, or a heteroaryl group.

4. The organic compound according to claim 1, wherein Ar represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorene group, a substituted or unsubstituted benzofluorene group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted triphenylenyl group.

5. The organic compound according to claim 1, wherein Ar represents one of the following substituents: ##STR00145## ##STR00146## ##STR00147## ##STR00148## ##STR00149## ##STR00150## ##STR00151##

6. The organic compound according to claim 1, wherein Ar represents one of the following substituents: ##STR00152##

7. The organic compound according to claim 1, wherein the organic compound is one of the following compounds: ##STR00153## ##STR00154## ##STR00155## ##STR00156## ##STR00157## ##STR00158## ##STR00159## ##STR00160## ##STR00161## ##STR00162## ##STR00163## ##STR00164## ##STR00165## ##STR00166## ##STR00167## ##STR00168## ##STR00169## ##STR00170## ##STR00171## ##STR00172## ##STR00173## ##STR00174## ##STR00175## ##STR00176## ##STR00177## ##STR00178## ##STR00179## ##STR00180## ##STR00181## ##STR00182## ##STR00183## ##STR00184## ##STR00185## ##STR00186## ##STR00187## ##STR00188## ##STR00189## ##STR00190## ##STR00191## ##STR00192## ##STR00193## ##STR00194## ##STR00195## ##STR00196## ##STR00197## ##STR00198## ##STR00199##

8. The organic compound according to claim 1, wherein the organic compound has one of the following formulas: ##STR00200## ##STR00201## ##STR00202## ##STR00203## ##STR00204##

9. The organic compound according to claim 1, wherein R.sub.1 to R.sub.4 are independently selected from the group consisting of a methyl group, a fluoride and ##STR00205##

10. An organic electroluminescence device comprising an anode, a cathode and one or more organic layers formed between the anode and the cathode, wherein at least one of the organic layers comprises the organic compound according to claim 1.

11. The organic electroluminescence device according to claim 10, wherein the organic layers comprise an emissive layer having a host, and wherein the organic compound is comprised as the host.

12. The organic electroluminescence device according to claim 10, wherein the organic layers comprise a hole blocking layer, and wherein the organic compound of claim 1 is comprised as the hole blocking layer.

13. The organic electroluminescence device according to claim 10, wherein the organic electroluminescence device is a lighting panel.

14. The organic electroluminescence device according to claim 10, wherein the organic electroluminescence device is a backlight panel.

Description

BRIEF DESCRIPTION OF THE DRAWINGS

[0008] FIG. 1 is a cross-sectional view of a first organic EL device according to a second embodiment of the present invention.

[0009] FIG. 2 is a cross-sectional view of an organic EL device without the host 340C of FIG. 1.

[0010] FIG. 3 is a cross-sectional view of a second organic EL device according to a third embodiment of the present invention.

DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0011] What probed into the invention is the organic compound and organic EL device using the organic compound. Detailed descriptions of the production, structure and elements will be provided as follows such that the invention can be fully understood. Obviously, the application of the invention is not confined to specific details familiar to those skilled in the art. On the other hand, the common elements and procedures that are known to everyone are not described in details to avoid unnecessary limits of the invention. Some preferred embodiments of the present invention will now be described in greater detail as follows. However, it should be recognized that the present invention can be practiced in a wide range of other embodiments besides those explicitly described, that is, this invention can also be applied extensively to other embodiments, and the scope of the present invention is expressly not limited except as specified in the accompanying claims.

[0012] In a first embodiment of the present invention, an organic compound may have the following formula (C):

##STR00004##

wherein P may be a divalent bridge selected from the group consisting of NAr, O, S, CR.sub.5R.sub.6 and SiR.sub.7R.sub.8. Q may be a single bond or a divalent bridge selected from the group consisting of NAr, O, S, CR.sub.5R.sub.6 and SiR.sub.7R.sub.8. At least one of X and Y may be NAr. X may be a divalent bridge selected from the group consisting of O, S, CR.sub.5R.sub.6 and SiR.sub.7R.sub.8 if X is not NAr. Y may be a divalent bridge selected from the group consisting of O, S, CR.sub.5R.sub.6 and SiR.sub.7R.sub.8 if Y is not NAr.

[0013] In formula (C), A may represent a substituted or unsubstituted fused ring hydrocarbons unit having two rings. B may represent a substituted or unsubstituted fused ring hydrocarbons unit having one or two rings.

[0014] Ar may represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. R.sub.1 to R.sub.8 may be independently selected from the group consisting of a hydrogen atom, a halide, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms; a substituted or unsubstituted arylamine group having 6 to 30 ring carbon atoms, and a substituted or unsubstituted heteroarylamine group having 5 to 30 ring carbon atoms. The alkyl group, aralkyl group, aryl group, heteroaryl group, arylamine group, or heteroarylamine group is substituted by, for example, a halogen, an alkyl group, an aryl group, or a heteroaryl group.

[0015] In a second embodiment of the present invention, a first organic EL device using the organic compound of formula (C) is disclosed. FIG. 1 is a cross-sectional view of the first organic EL device. Referring to FIG. 1, the first organic EL device 510 may comprise the organic compound of formula (C) as a host 340C of an emissive layer 340E.

[0016] FIG. 2 is a cross-sectional view of an organic EL device without the organic compound of formula (C) (without 340C of FIG. 1). Referring to FIG. 2, the organic EL device 400 may have a driving voltage of about 5.1 V, a current efficiency of about 18 cd/A, or a half-life of about 350 hours.

[0017] Referring to FIG. 1, by comprising the organic compound of formula (C) as the host 340C, the first organic EL device 510 may have a driving voltage lower than that of the organic EL device 400 (FIG. 2). Moreover, by comprising the organic compound of formula (C) as the host 340C, the first organic EL device 510 of FIG. 1 may have a current efficiency higher than that of the organic EL device 400 (FIG. 2). Furthermore, by comprising the organic compound of formula (C) as the host 340C, the first organic EL device 510 of FIG. 1 may have a half-life longer than that of the organic EL device 400 (FIG. 2).

[0018] As the host 340C of the first organic EL device 510 of FIG. 1, the organic compound of formula (C) may lower the driving voltage to be about 2.8 V to about 4.5 V. Moreover, the organic compound of formula (C) may increase the current efficiency to be 25 cd/A to about 45 cd/A. Furthermore, the organic compound of formula (C) may increase the half-life to be about 430 hours to about 1000 hours.

[0019] In a third embodiment of the present invention, a second organic EL device using the organic compound of formula (C) is disclosed. FIG. 3 is a cross-sectional view of the second organic EL device. Referring to FIG. 3, the second organic EL device 520 may comprise the organic compound of formula (C) as a hole blocking layer 350C.

[0020] FIG. 2 is a cross-sectional view of an organic EL device without the organic compound of formula (C) (without 350C of FIG. 3). Referring to FIG. 2, the organic EL device 400 may have a driving voltage of about 5.1 V, a current efficiency of about 18 cd/A, or a half-life of about 350 hours.

[0021] Referring to FIG. 3, by comprising the organic compound of formula (C) as the hole blocking layer 350C, the second organic EL device 520 may have a driving voltage lower than that of the organic EL device 400 (FIG. 2). Moreover, by comprising the organic compound of formula (C) as the hole blocking layer 350C, the second organic EL device 520 of FIG. 3 may have a current efficiency higher than that of the organic EL device 400 (FIG. 2). Furthermore, by comprising the organic compound of formula (C) as the hole blocking layer 350C, the second organic EL device 520 of FIG. 3 may have a half-life longer than that of the organic EL device 400 (FIG. 2).

[0022] Referring to FIG. 3, as the hole blocking layer 350C of the second organic EL device 520, the organic compound of formula (C) may lower the driving voltage to be about 4.0 V to about 4.9 V. Moreover, the organic compound of formula (C) may increase the current efficiency to be about 20 cd/A to about 27 cd/A. Furthermore, the organic compound of formula (C) may increase the half-life to be about 380 hours to about 520 hours.

[0023] In formula (C), Ar may also represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorene group, a substituted or unsubstituted benzofluorene group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted triphenylenyl group.

[0024] The organic compound of the present invention may also have one of the following formula (3) to formula (26):

##STR00005## ##STR00006## ##STR00007## ##STR00008## ##STR00009## ##STR00010## ##STR00011## ##STR00012##

The same definition as described in the paragraph [0011] to paragraph [0027].

[0025] In formula (C), Ar may represent one of the following substituents:

##STR00013## ##STR00014## ##STR00015## ##STR00016## ##STR00017## ##STR00018##

[0026] The organic compound of the present invention may also have one of the following formulas:

##STR00019## ##STR00020## ##STR00021## ##STR00022## ##STR00023##

[0027] In formula (C), R.sub.1 to R.sub.4 may be independently selected from the group consisting of a methyl group, a fluoride and

##STR00024##

[0028] The organic compound of the present invention may be one of the following compounds:

##STR00025## ##STR00026## ##STR00027## ##STR00028## ##STR00029## ##STR00030## ##STR00031## ##STR00032## ##STR00033## ##STR00034## ##STR00035## ##STR00036## ##STR00037## ##STR00038## ##STR00039## ##STR00040## ##STR00041## ##STR00042## ##STR00043## ##STR00044## ##STR00045## ##STR00046## ##STR00047## ##STR00048## ##STR00049## ##STR00050## ##STR00051## ##STR00052## ##STR00053## ##STR00054## ##STR00055## ##STR00056## ##STR00057## ##STR00058## ##STR00059## ##STR00060## ##STR00061## ##STR00062## ##STR00063## ##STR00064## ##STR00065## ##STR00066## ##STR00067## ##STR00068## ##STR00069## ##STR00070## ##STR00071##

[0029] Referring to FIG. 1, the first organic EL device 510 may comprise an anode 310, a cathode 380 and one or more organic layers 320, 330, 340E, 350, 360, 370 formed between the anode 310 and the cathode 380. From the bottom to the top, the one or more organic layers may comprise a hole injection layer 320, a hole transport layer 330, an emissive layer 340E, a hole blocking layer 350, an electron transport layer 360 and an electron injection layer 370.

[0030] The emissive layer 340E may comprise a 15% dopant D1 and the organic compound of formula (C) 340C doped with the dopant D1. The dopant D1 may be a green guest material for tuning the wavelength at which the emissive layer 340E emits light, so that the color of emitted light may be green. The organic compound of formula (C) may be a host 340C of the emissive layer 340E.

[0031] FIG. 2 is a cross-sectional view of an organic EL device without the organic compound of formula (C). Referring to FIG. 2, the organic EL device 400 may comprise an anode 310, a cathode 380 and one or more organic layers 320, 330, 340, 350, 360, 370 formed between the anode 310 and the cathode 380. From the bottom to the top, the one or more organic layers may comprise a hole injection layer 320, a hole transport layer 330, an emissive layer 340, a hole blocking layer 350, an electron transport layer 360 and an electron injection layer 370. The emissive layer 340 may comprise a 15% dopant D1 and an organic compound H1 doped with the dopant D1. The dopant D1 may be a green guest material. The organic compound H1 is a host of the emissive layer 340.

[0032] To those organic EL devices of FIG. 1 and FIG. 2, EL spectra and CIE coordination are measured by using a PR650 spectra scan spectrometer. Furthermore, the current/voltage, luminescence/voltage, and yield/voltage characteristics are taken with a Keithley 2400 programmable voltage-current source. The above-mentioned apparatuses are operated at room temperature (about 25 C.) and under atmospheric pressure.

[0033] The I-V-B (at 1000 nits) test reports of those organic EL devices of FIG. 1 and FIG. 2 may be summarized in Table 1 below. The half-life is defined as the time that the initial luminance of 1000 cd/m.sup.2 has dropped to half.

TABLE-US-00001 TABLE 1 (The Comp. is short for Compound) Driving Current Host Voltage Efficiency CIE Half-life (H1 or 340C) Dopant (V) (cd/A) (y) (hours) H1 D1 5.1 18 0.53 350 Comp. 3 D1 3.9 34 0.55 650 Comp. 5 D1 3.8 36 0.54 700 Comp. 6 D1 3.7 37 0.53 720 Comp. 7 D1 4.4 28 0.52 480 Comp. 10 D1 4.0 33 0.55 630 Comp. 22 D1 4.5 27 0.54 440 Comp. 26 D1 3.7 36 0.54 680 Comp. 27 D1 2.9 44 0.54 900 Comp. 37 D1 3.8 35 0.53 690 Comp. 48 D1 4.6 25 0.56 430 Comp. 59 D1 3.2 42 0.55 920 Comp. 74 D1 2.9 45 0.53 1000 Comp. 75 D1 3.0 44 0.56 960 Comp. 86 D1 3.9 34 0.54 660 Comp. 112 D1 4.4 28 0.54 520 Comp. 135 D1 4.3 28 0.52 500 Comp. 141 D1 4.6 27 0.56 450 Comp. 145 D1 4.5 26 0.54 430 Comp. 155 D1 2.8 45 0.53 980 Comp. 171 D1 3.1 43 0.52 900 Comp. 189 D1 3.0 44 0.54 920 Comp. 198 D1 3.1 43 0.53 900 Comp. 229 D1 3.8 36 0.55 650 Comp. 235 D1 3.9 35 0.53 660

[0034] According to Table 1, in the first organic EL device 510, the organic compound of formula (C) comprised as a host 340C of FIG. 1 exhibits performance better than a prior art organic EL material (H1).

[0035] A method of producing the first organic EL device 510 of FIG. 1 and the organic EL device 400 of FIG. 2 is described. ITO-coated glasses with 912 ohm/square in resistance and 120160 nm in thickness are provided (hereinafter ITO substrate) and cleaned in a number of cleaning steps in an ultrasonic bath (e.g. detergent, deionized water).

[0036] Before vapor deposition of the organic layers, cleaned ITO substrates may be further treated by UV and ozone. All pre-treatment processes for ITO substrate are under clean room (class 100), so that an anode 310 may be formed.

[0037] One or more organic layers 320, 330, 340 (FIG. 2), 340E (FIG. 1), 350, 360, 370 are applied onto the anode 310 in order by vapor deposition in a high-vacuum unit (10.sup.7 Torr), such as resistively heated quartz boats. The thickness of the respective layer and the vapor deposition rate (0.10.3 nm/sec) are precisely monitored or set with the aid of a quartz-crystal monitor. It is also possible, as described above, each of the organic layers may comprise more than one organic compound. For example, an emissive layer 340E or 340 may be formed of a dopant and a host doped with the dopant. An emissive layer 340E or 340 may also be formed of a co-host and a host co-deposited with the co-host. This may be successfully achieved by co-vaporization from two or more sources. Accordingly, the compounds for the organic layers of the present invention are thermally stable.

[0038] Referring to FIG. 1 and FIG. 2, onto the anode 310, Dipyrazino[2,3-f:2,3-]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN) may be applied to form a hole injection layer 320 having a thickness of about 20 nm in the organic EL device 510 or 400. N,N-Bis(naphthalene-1-yl)-N,N-bis(phenyl)-benzidine (NPB) may be applied to form a hole transporting layer 330 having a thickness of about 110 nm. Referring to FIG. 1 and FIG. 2, in the organic EL device 510 (FIG. 1) or 400 (FIG. 2), an emissive layer 340E or 340 may be formed to have a thickness of about 30 nm.

[0039] Referring to FIG. 2, in the organic EL device 400, 12-(4,6-diphenyl-1,3,5-triazin-2-yl)-10,10-dimethyl-10,12-dihydrophenanthro[9,10:5,6]indeno[2,1-b]carbazole (i.e., H1 of paragraph [0002]) may be applied to form a host H1 of an emissive layer 340 of FIG. 2. The emissive layer 340 may further comprise bis(2-phenylpyridinato)(2,4-diphenylpyridinato)iridium(III) as a dopant D1, also a green guest of the emissive layer 340. The doped emissive layer 340 may have a thickness of about 30 nm.

[0040] On the emissive layer 340, a compound HB1 may be a hole blocking material (HBM) to form a hole blocking layer 350. 2-(naphthalen-1-yl)-9-(4-(1-(4-(10-(naphthalene-2-yl)anthracen-9-yl)-phenyl)-1H-benzo[d]imidazol-2-yl)phenyl)-1,10-phenanthroline (ET1) may be applied as an electron transporting material to co-deposit with 8-hydroxyquinolato-lithium (LiQ) at a ratio of 1:1, thereby forming an electron transporting layer (ETL) 360 of the organic EL device 510 or 400. The electron transporting layer (ETL) 360 may have a thickness of about 35 nm. The organic compounds ET1, HB1, D1, NPB and HAT-CN for producing the organic EL device 400 or 510 in this invention may have the formulas as follows:

##STR00072##

[0041] Referring to FIG. 1 and FIG. 2, the organic EL device 510 or 400 may further comprise a low work function metal, such as Al, Mg, Ca, Li or K, as a cathode 380 by thermal evaporation. A low work function metal may help electrons injecting the electron transporting layer 360 from cathode 380. The cathode 380 may have a thickness of about 160 nm. Between the cathode 380 and the electron transporting layer 360, a thin electron injecting layer 370 of LiQ having a thickness of about 1 nm is introduced, to reduce the electron injection barrier and to improve the performance of the organic EL device 510 or 400. The material of the electron injecting layer 370 may alternatively be metal halide or metal oxide with low work function, such as LiF, MgO, or Li.sub.2O.

[0042] In a third embodiment of the present invention, a second organic EL device using the organic compound of formula (C) is disclosed. The method of producing the second organic EL device 520 of FIG. 3 is substantially the same as the method of producing the organic EL device 400 of FIG. 2. The difference is that the hole blocking layer (HBL) 350C of FIG. 3 is made by using the organic compound of formula (C), rather than HB1.

[0043] To those organic EL devices of FIG. 3 and FIG. 2, EL spectra and CIE coordination are measured by using a PR650 spectra scan spectrometer. Furthermore, the current/voltage, luminescence/voltage, and yield/voltage characteristics are taken with a Keithley 2400 programmable voltage-current source. The above-mentioned apparatuses are operated at room temperature (about 25 C.) and under atmospheric pressure.

[0044] The I-V-B (at 1000 nits) test reports of those organic EL devices of FIG. 3 and FIG. 2 may be summarized in Table 2 below. The half-life of the fluorescent green-emitting organic EL device 520 or 400 is defined as the time that the initial luminance of 1000 cd/m has dropped to half.

TABLE-US-00002 TABLE 2 (The Comp. is short for Compound) Material Driving Current Material for for Voltage Efficiency CIE Half-life HBL 350 or 350C ETL 360 (V) (cd/A) (y) (hours) HB1 ET1 5.1 18 0.53 350 Comp. 13 ET1 4.3 23 0.52 430 Comp. 23 ET1 4.4 24 0.55 440 Comp. 34 ET1 4.0 27 0.56 520 Comp. 39 ET1 4.0 26 0.54 510 Comp. 41 ET1 4.3 24 0.55 430 Comp. 55 ET1 4.4 23 0.52 420 Comp. 69 ET1 4.1 25 0.55 500 Comp. 83 ET1 4.7 21 0.54 400 Comp. 108 ET1 4.2 25 0.53 480 Comp. 115 ET1 4.5 22 0.52 410 Comp. 138 ET1 4.8 22 0.54 380 Comp. 148 ET1 4.9 20 0.52 380 Comp. 154 ET1 4.8 21 0.54 390 Comp. 214 ET1 4.0 27 0.53 510 Comp. 231 ET1 4.1 26 0.55 500

[0045] According to Table 2, in the second organic EL device 520, the organic compound of formula (C) comprised as a hole blocking layer 350C of FIG. 3 exhibits performance better than a prior art hole blocking material (HB1 as a HBL 350 of FIG. 2).

[0046] Referring to FIG. 1 or FIG. 3, the organic EL device 510 or 520 of the present invention may alternatively be alighting panel or a backlight panel.

[0047] Detailed preparation of the organic compounds of the present invention will be clarified by exemplary embodiments below, but the present invention is not limited thereto. EXAMPLES 1 to 23 show the preparation of the organic compounds of the present invention.

Example 1

Synthesis of 9-bromo-7H-benzo[c]phenoxazine

[0048] ##STR00073##

[0049] 10 g (42.9 mmol) of 7H-benzo[c]phenoxazine was dissolved in 200 ml of acetic acid, and the mixture was allowed to cool to 0 C. 6.9 g (42.9 mmol) of bromine was dropped into the mixture, and then the mixture was stirred at room temperature for 12 hrs. After the reaction finished, the mixture was extracted with dichloromethane/H.sub.2O, and the organic layer was removed under reduced pressure, and the crude product was purified by column chromatography, yielding 10.2 g of 9-bromo-7H-benzo[c]phenoxazine as yellow solid (76.2%). .sup.1H NMR (CDCl.sub.3, 400 MHz): chemical shift (ppm) 8.01 (d, 2H), 7.56 (dd, 1H), 7.43 (dd, 1H), 7.42-7.39 (m, 1H), 7.07-7.02 (m, 2H), 6.77-6.73 (m, 2H), 4.11 (s, H).

Synthesis of 9-bromo-7-phenyl-7H-benzo[c]phenoxazine

[0050] ##STR00074##

[0051] A mixture of 10.2 g (32.7 mmol) of 9-bromo-7H-benzo[c]phenoxazine, 6.7 g (32.7 mmol) of iodobenzene, 0.15 g (0.65 mmol) of Pd(OAc).sub.2, 4.7 g (49.1 mmol) of sodium tert-butoxide, and 200 ml of o-xylene was degassed and placed under nitrogen, and then heated to reflux for 12 hrs. After the reaction finished, the mixture was allowed to cool to room temperature. Subsequently, the solvent was removed under reduced pressure, and the crude product was purified by column chromatography, yielding 10.3 g of 9-bromo-7-phenyl-7H-benzo[c]phenoxazine as yellow solid (81.1%). .sup.1H NMR (CDCl.sub.3, 400 MHz): chemical shift (ppm) 7.99 (d, 2H), 7.54 (dd, 1H), 7.39-7.34 (m, 2H), 7.22-7.19 (m, 2H), 7.02 (d, 1H), 6.91 (d, 1H), 6.81-6.77 (m, 2H), 6.66-6.61 (m, 3H).

Synthesis of 7-phenyl-9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7H-benzo[c]phenoxazine

[0052] ##STR00075##

[0053] A mixture of 10.3 g (26.5 mmol) of 9-bromo-7-phenyl-7H-benzo[c]-phenoxazine, 8.08 g (31.8 mmol) of bis(pinacolato)diboron, 0.6 g (0.5 mmol) of Pd(Ph.sub.3).sub.4, 3.9 g (39.8 mmol) of potassium acetate, and 150 ml of 1,4-dioxane was degassed and placed under nitrogen, and then heated to reflux for 12 hrs. After the reaction finished, the mixture was allowed to cool to room temperature. Subsequently, the solvent was removed under reduced pressure, and the crude product was purified by column chromatography, yielding 9 g of 7-phenyl-9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7H-benzo[c]phenoxazine as white solid (78%). .sup.1H NMR (CDCl.sub.3, 400 MHz): chemical shift (ppm) 8.01 (d, 2H), 7.55 (dd, 1H), 7.42-7.36 (m, 2H), 7.23-7.20 (m, 2H), 7.07-7.03 (m, 2H), 6.93 (d, 1H), 6.82-6.79 (m, 1H), 6.67-6.63 (m, 3H), 1.26 (s, 12H).

Synthesis of 9-(9-(naphthalen-2-yl)-9H-carbazol-3-yl)-7-phenyl-7H-benzo[c]phenoxazine (Compound 205)

[0054] ##STR00076##

[0055] A mixture of 9 g (20.7 mmol) of 7-phenyl-9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7H-benzo[c]phenoxazine, 7.7 g (20.7 mmol) of 3-bromo-9-(naphthalen-2-yl)-9H-carbazole, 0.48 g (0.04 mmol) of Pd(Ph.sub.3).sub.4, 20.7 ml of 2M Na.sub.2CO.sub.3, 100 ml of EtOH and 200 ml of toluene was degassed and placed under nitrogen, and then heated to reflux for 12 hrs. After the reaction finished, the mixture was allowed to cool to room temperature. Subsequently, the solvent was removed under reduced pressure, and the crude product was purified by column chromatography, yielding 8.9 g of 9-(9-(naphthalen-2-yl)-9H-carbazol-3-yl)-7-phenyl-7H-benzo[c]phenoxazine as white solid (71.7%). .sup.1H NMR (CDCl.sub.3, 400 MHz): chemical shift (ppm) 8.20 (d, 1H), 8.13 (d, 1H), 8.03-7.96 (m, 6H), 7.84 (s, H), 7.76 (s, H), 7.65-7.59 (m, 3H), 7.50-7.46 (m, 2H), 7.38-7.32 (m, 4H), 7.22-7.18 (m, 2H), 7.09-7.04 (m, 2H), 6.95 (d, 1H), 6.86-6.81 (m, 2H), 6.65 (d, 2H).

Example 2

Synthesis of 7-phenyl-9-(10-phenyl-10H-phenoxazin-3-yl)-7H-benzo[c]phenoxazine (Compound 213)

[0056] ##STR00077##

[0057] A mixture of 5 g (11.5 mmol) of 7-phenyl-9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7H-benzo[c]phenoxazine, 3.9 g (11.5 mmol) of 3-bromo-10-phenyl-10H-phenoxazine, 0.24 g (0.02 mmol) of Pd(Ph.sub.3).sub.4, 11.5 ml of 2M Na.sub.2CO.sub.3, 50 ml of EtOH and 100 ml of toluene was degassed and placed under nitrogen, and then heated to reflux for 12 hrs. After the reaction finished, the mixture was allowed to cool to room temperature. Subsequently, the solvent was removed under reduced pressure, and the crude product was purified by column chromatography, yielding 4.4 g of 7-phenyl-9-(10-phenyl-10H-phenoxazin-3-yl)-7H-benzo[c]phenoxazine as white solid (68%). .sup.1H NMR (CDCl.sub.3, 400 MHz): chemical shift (ppm) 8.03 (d, 2H), 7.58 (m, 1H), 7.45-7.38 (m, 2H), 7.29-7.21 (m, 6H), 7.13-7.08 (m, 2H), 6.98-6.92 (m, 3H), 6.85-6.79 (m, 4H), 6.68-6.61 (m, 6H).

Example 3

Synthesis of 7-phenyl-9-(5-phenyl-5H-benzo[b]carbazol-2-yl)-7H-benzo[c]phenoxazine (Compound 221)

[0058] ##STR00078##

[0059] A mixture of 5 g (11.5 mmol) of 7-phenyl-9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7H-benzo[c]phenoxazine, 4.3 g (11.5 mmol) of 2-bromo-5-phenyl-5H-benzo[b]carbazole, 0.24 g (0.02 mmol) of Pd(Ph).sub.4, 11.5 ml of 2M Na.sub.2CO.sub.3, 50 ml of EtOH and 100 ml of toluene was degassed and placed under nitrogen, and then heated to reflux for 12 hrs. After the reaction finished, the mixture was allowed to cool to room temperature. Subsequently, the solvent was removed under reduced pressure, and the crude product was purified by column chromatography, yielding 4.9 g of 7-phenyl-9-(5-phenyl-5H-benzo[b]carbazol-2-yl)-7H-benzo[c]phenoxazine as white solid (71%). .sup.1H NMR (CDCl.sub.3, 400 MHz): chemical shift (ppm) 8.19-8.15 (m, 3H), 8.01-7.95 (m, 3H), 7.79 (s, 1H), 7.69-7.65 (m, 2H), 7.57-7.50 (m, 6H), 7.43-7.36 (m, 4H), 7.22-7.20 (m, 2H), 7.10 (d, 1H), 7.03 (d, 1H), 6.94 (d, 1H), 6.83-6.78 (m, 2H), 6.61 (d, 2H).

Example 4

Synthesis of 7-phenyl-9-(7-phenyl-7H-benzo[c]phenothiazin-9-yl)-7H-benzo[c]phenoxazine (Compound 236)

[0060] ##STR00079##

[0061] A mixture of 5 g (11.5 mmol) of 7-phenyl-9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7H-benzo[c]phenoxazine, 4.1 g (11.5 mmol) of 2-bromo-5-phenyl-5H-benzo[b]carbazole, 0.24 g (0.02 mmol) of Pd(Ph.sub.3).sub.4, 11.5 ml of 2M Na.sub.2CO.sub.3, 50 ml of EtOH and 100 ml of toluene was degassed and placed under nitrogen, and then heated to reflux for 12 hrs. After the reaction finished, the mixture was allowed to cool to room temperature. Subsequently, the solvent was removed under reduced pressure, and the crude product was purified by column chromatography, yielding 4.3 g of 7-phenyl-9-(7-phenyl-7H-benzo[c]phenothiazin-9-yl)-7H-benzo[c]-phenoxazine as white solid (59.1%). .sup.1H NMR (CDCl.sub.3, 400 MHz): chemical shift (ppm) 8.18 (d, 2H), 8.01-7.97 (d, 2H), 7.69-7.66 (m, 2H), 7.53-7.51 (m, 1H), 7.43-7.37 (m, 2H), 7.25-7.18 (m, 6H), 7.11 (d, 1H), 7.02-6.96 (m, 4H), 6.88-6.81 (m, 4H), 6.65 (d, 4H).

Example 5-23

[0062] A series of intermediates and the product compounds are synthesized analogously, as follows.

TABLE-US-00003 Ex. Intermediate III Intermediate IV Product Yield 5 [00080] [00081] [00082] 69% 6 [00083] [00084] [00085] 54% 7 [00086] [00087] [00088] 48% 8 [00089] [00090] [00091] 62% 9 [00092] [00093] [00094] 57% 10 [00095] [00096] [00097] 64% 11 [00098] [00099] [00100] 62% 12 [00101] [00102] [00103] 51% 13 [00104] [00105] [00106] 48% 14 [00107] [00108] [00109] 41% 15 [00110] [00111] [00112] 49% 16 [00113] [00114] [00115] 44% 17 [00116] [00117] [00118] 51% 18 [00119] [00120] [00121] 45% 19 [00122] [00123] [00124] 42% 20 [00125] [00126] [00127] 51% 21 [00128] [00129] [00130] 41% 22 [00131] [00132] [00133] 50% 23 [00134] [00135] [00136] 47%

[0063] When Q of formula (C) is a single bond, the organic compound may have the following formula:

##STR00137##

The same definition as described in the paragraph [0011] to paragraph [0027].

[0064] Obviously, many modifications and variations are possible in light of the above teachings. It is therefore to be understood that within the scope of the appended claims the present invention can be practiced otherwise than as specifically described herein. Although specific embodiments have been illustrated and described herein, it is obvious to those skilled in the art that many modifications of the present invention may be made without departing from what is intended to be limited solely by the appended claims.