A photoconductive imaging member comprised of a charge transport layer comprised of an indolocarbazole represented by the Formulas (Ia), (IIa), (IIIa), (IVa), (Va), or (VIa); or optionally mixtures thereof: ##STR1## wherein R and R' are independently selected from the group consisting of a hydrogen atom, a halogen atom, alkyl, alkoxyl, and aryl; m and n are numbers of from 0 to 4; R.sup.1 and R.sup.2 are independently selected from the group consisting of alkyl, aryl, vinyl, and diarylaminoaryl; R.sup.3 and R.sup.4 are an atom of hydrogen, alkyl, alkoxy, aryl, or halogen, and p is a number of from 1 to 3.

Illustrated in copending applications U.S. Ser. No. 942,598; U.S. Ser. No. 
942,882; and U.S. Ser. No. 942,647, and filed currently herewith, the 
disclosures of each application being totally incorporated herein by 
reference, are El devices containing, for example, indolocarbazoles, 
amines thereof, and processes thereof. 
Also, in U.S. Pat. No. 5,473,064, the disclosure of which is totally 
incorporated herein by reference, there is illustrated a process for the 
preparation of hydroxygallium phthalocyanine Type V, essentially free of 
chlorine. 
Also, illustrated in copending applications and patents U.S. Pat. No. 
5,763,110. U.S. Ser. No. 707,260, U.S. Ser. No. 807,488, U.S. Ser. No. 
807,489, U.S. Ser. No. 807,510 and U.S. Ser. No. 829,398, the disclosures 
of each being totally incorporated herein by reference, are EL devices. 
In U.S. Pat. No. 5,645,965, the disclosure of which is totally incorporated 
herein by reference, there are illustrated photoconductive imaging members 
with perylenes. 
The appropriate components, such as the substrates, photogenerating 
components, resin binders, adhesive layers, silane layers, protective 
overcoatings, and the like, of the aforementioned patents and patent 
applications, and the prior art references cited therein, can be selected 
as components for the imaging members of the present application in 
embodiments thereof. 
BACKGROUND OF THE INVENTION 
This invention is generally directed to indolocarbazole compounds, 
photoconductive imaging members thereof, organic charge, especially hole 
transports, and also in embodiments organic hole transport molecules that 
are suitable for layered electroluminescent (EL) devices. In embodiments, 
the present invention is directed to organic hole transport molecules 
which enable the design and fabrication of thermally and morphologically 
stable hole transport components, and which components possess enhanced 
operational stability, and thus long operational life. More specifically, 
the present invention in embodiments relates to indolocarbazole hole 
transport compounds and processes thereof, and which indolocarbazole 
compounds can be selected for the preparation of thermally and 
morphologically stable thin film hole transport layers for photoconductive 
imaging members. The photoconductive imaging members can be comprised of 
the indolocarbazole compounds as charge transport components, and more 
specifically, wherein the imaging members are comprised of a supporting 
substrate, such as a metal, or a metallized polymer like aluminized 
MYLAR.RTM., a photogenerating layer of, for example, hydroxygallium 
phthalocyanines, titanyl phthalocyanines, perylenes, especially BZP, 
chlorindinium phthalocyanines, selenium, especially trigonal selenium, and 
the like. Examples of supporting substrates, photogenerating components, 
and other components for the imaging member are illustrated in a number of 
U.S. Pat. Nos., such as 4,265,990 and 5,645,965, the disclosures of which 
are totally incorporated herein by reference. 
The imaging members of the present invention in embodiments exhibit 
excellent cyclic stability, independent layer discharge, and substantially 
no adverse changes in performance over extended time periods. The 
aforementioned photoresponsive, or photoconductive imaging members can be 
negatively charged when the photogenerating layer is situated between the 
hole transport layer and the substrate. Processes of imaging, especially 
xerographic imaging and printing, including digital, are also encompassed 
by the present invention. 
More specifically, the layered photoconductive imaging members can be 
selected for a number of different known imaging and printing processes 
including, for example, electrophotographic imaging processes, especially 
xerographic imaging and printing processes wherein negatively charged or 
positively charged images are rendered visible with toner compositions of 
an appropriate charge polarity. The imaging members as indicated herein 
are in embodiments sensitive in the wavelength region of, for example, 
from about 550 to about 900 nanometers, and in particular, from about 700 
to about 850 nanometers, thus diode lasers can be selected as the light 
source. Moreover, the imaging members of the present invention are 
preferably useful in color xerographic applications where several color 
printings can be achieved in a single pass. 
PRIOR ART 
Layered photoresponsive imaging members have been described in a number of 
U.S. patents, such as U.S. Pat. No. 4,265,990, the disclosure of which is 
totally incorporated herein by reference, wherein there is illustrated an 
imaging member comprised of a photogenerating layer, and an aryl amine 
hole transport layer. Examples of photogenerating layer components include 
trigonal selenium, metal phthalocyanines, vanadyl phthalocyanines, and 
metal free phthalocyanines. Additionally, there is described in U.S. Pat. 
No. 3,121,006 a composite xerographic photoconductive member comprised of 
finely divided particles of a photoconductive inorganic compound dispersed 
in an electrically insulating organic resin binder. The binder materials 
disclosed in the '006 patent comprise a material which is incapable of 
transporting for any significant distance injected charge carriers 
generated by the photoconductive particles. 
Also, in U.S. Pat. No. 4,555,463, the disclosure of which is totally 
incorporated herein by reference, there is illustrated a layered imaging 
member with a chloroindium phthalocyanine photogenerating layer. In U.S. 
Pat. No. 4,587,189, the disclosure of which is totally incorporated herein 
by reference, there is illustrated a layered imaging member with, for 
example, a BZP perylene, pigment photogenerating component. Both of the 
aforementioned patents disclose an aryl amine component as a hole 
transport layer. 
Illustrated in U.S. Pat. No. 5,493,016, the disclosure of which is totally 
incorporated herein by reference, are imaging members comprised of a 
supporting substrate, a photogenerating layer of hydroxygallium 
phthalocyanine, a charge transport layer, a photogenerating layer of BZP 
perylene, which is preferably a mixture of bisbenzimidazo(2,1-a-1',2'-b) 
anthra(2,1,9-def:6,5,10-d'e'f')diisoquinoline-6,11-dione and 
bisbenzimidazo (2,1-a:2',1'-a)anthra(2,1,9-def:6,5,10-d'e'f')diisoquinolin 
e-10, 21-dione, reference U.S. Pat. No. 4,587,189, the disclosure of which 
is totally incorporated herein by reference; and as a top layer a second 
charge transport layer U.S. Pat. No. 4,587,189, the disclosure of which is 
totally incorporated herein by reference, illustrates photoconductive 
imaging members with certain perylenes; and U.S. Pat. No. 5,482,811, the 
disclosure of which is totally incorporated herein by reference, 
illustrated photoconductive imaging members with Type V hydroxygallium 
phthalocyanine. 
The disclosures of all of the aforementioned copending applications and 
patents are totally incorporated herein by reference. 
SUMMARY OF THE INVENTION 
It is a feature of the present invention to provide imaging members thereof 
with many of the advantages illustrated herein. 
Another feature of the present invention relates to the provision of 
improved layered photoresponsive imaging members with photosensitivity to 
near infrared radiations. 
It is yet another feature of the present invention to provide improved 
layered photoresponsive imaging members with a sensitivity to visible 
light, and which members possess improved electricals and improved coating 
characteristics, and wherein the charge transport molecules do not 
diffuse, or there is minimum diffusion thereof into the photogenerating 
layer. 
Moreover, another feature of the present invention relates to the provision 
of improved layered photoresponsive imaging members with photosensitivity 
to near infrared radiations, for example from about 750 to about 950 
nanometers, and to visible light of a wavelength of from about 500 to 
about 800 nanometers. 
In embodiments, the present invention relates to the provision of imaging 
members, and more specifically, the photoconductive imaging members are 
comprised of an optional supporting substrate, a photogenerating layer of, 
for example, hydroxygallium phthalocyanine, BZP perylene, and the like, 
reference U.S. Pat. No. 4,587,189, and an indolocarbazole charge transport 
layer. 
In embodiments, the present invention relates to a photoconductive imaging 
member comprised of a charge transport layer comprised of an 
indolocarbazole represented by the Formulas (Ia), (IIa), (IIIa), (IVa), 
(Va), or (VIa); or optionally mixtures thereof: 
##STR2## 
wherein R and R' are independently selected from the group consisting of a 
hydrogen atom, a halogen atom, alkyl, alkoxyl, and aryl; m and n are 
numbers of from 0 to 4; R.sup.1 and R.sup.2 are independently selected 
from the group consisting of alkyl, aryl, vinyl, and diarylaminoaryl; 
R.sup.3 and R.sup.4 are an atom of hydrogen, alkyl, alkoxy, aryl, or 
halogen, and p is a number of from 1 to 3; a member wherein aryl is a 
fused aromatic ring; a member wherein said fused ring is benzo; a member 
wherein alkyl contains from 1 to about 25 carbon atoms, alkoxy contains 
from 1 to about 25 carbon atoms, and aryl contains from 6 to about 30 
carbon atoms; a member wherein alkyl contains from 1 to about 10 carbon 
atoms, alkoxy contains from 2 to about 12carbon atoms, and aryl contains 
from 6 to about 18 carbon atoms; a member wherein alkyl contains from 1 to 
about 6 carbon atoms, and alkoxy contains from 1 to about 6 carbon atoms; 
a member wherein alkyl is methyl, ethyl, propyl, butyl, pentyl, heptyl, or 
hexyl, and wherein alkoxy is methoxy, ethoxy, propoxy, butoxy, pentoxy, or 
heptoxy; a member wherein halogen is a chlorine, bromine, fluorine, or 
iodine atom; a member wherein aryl is phenyl; a member wherein m and n are 
the numbers 1, 2, 3, or 4; a member wherein R and R' are hydrogen atoms, 
or alkyl, and R.sup.1 and R.sup.2 are aryl; a member wherein R.sup.3 and 
R.sup.4 are hydrogen atoms; a member wherein R.sup.1 and R.sup.2 are 
independently selected from the group consisting of phenyl, naphthyl, and 
biphenyl; a member wherein R.sup.1 or R.sup.2 are diarylaminoaryl as 
represented by Formula (VII): 
##STR3## 
wherein A is arylene, and Ar.sup.1 and Ar.sup.2 are aryl; a member wherein 
A is selected from the group consisting of phenylene and biphenylene, and 
Ar.sup.1 and Ar.sup.2 are aryl groups independently selected from the 
group consisting of phenyl, tolyl, xylyl, chlorophenyl, alkoxyphenyl, and 
naphthyl; a member wherein indolocarbazole (Ia), or (IIa) is selected; a 
member wherein said indolocarbazole is 
5,11-di-m-tolyl-5,11-dihydroindolo3,2-b!carbazole, 
5,11-bis(3,4-dimethylphenyl)-5,11-dihydroindolo3,2-b!carbazole, 
5,11-di-1-naphthyl-5,11-dihydroindolo3,2-b!carbazole, 
5,11-bis(3-methoxyphenyl) -5,11-dihydroindolo3,2-b!carbazole, or 
5,11-bis4'-(3-methyldiphenylamino)-1,1'-biphenyl-4-yl!-5,11-dihydroindolo 
3,2-b!carbazole; a member comprised of a supporting substrate, a 
photogenerating layer, and a charge transport layer, and wherein said 
charge transport layer is comprised of said indolocarbazoles; a member 
wherein said photogenerating layer is comprised of photogenerating 
components of selenium, metal free phthalocyanines, metal phthalocyanines, 
hydroxygallium phthalocyanines, perylenes, or titanyl phthalocyanines; a 
member wherein said photogenerating layer is situated between the 
substrate and the charge transport layer, and said charge transport layer 
components are dispersed in a resin binder; a process for the preparation 
of indolocarbazoles represented by Formulas (Ia) through (VIa), which 
comprises the condensation of a dihydroindolocarbazole (Ib), (IIb), 
(IIIb), (IVb), (Vb), or (VIb), with an aryl halide in the presence of a 
copper catalyst: 
##STR4## 
wherein R and R' are independently selected from the group consisting of 
hydrogen, halogen, alkyl, alkoxyl, diarylaminoaryl, and aryl; m and n are 
numbers of from 0 to 4; R.sup.3 and R.sup.4 are hydrogen, alkyl, alkoxy, 
aryl, or halogen, and p is a number of from 1 to 3; a process wherein said 
condensation is conducted by heating at a reaction temperature of from 
about 120.degree. C. to about 250.degree. C., and said 
dihydroindolocarbazole is selected from the group consisting of 
5,11-dihydroindolo3,2-b!carbazole, 5,7-dihydroindolo2,3-b!carbazole, 
5,12-dihydroindolo3,2-c!carbazole, 5,10-dihydroindolo3,2-a!carbazole, 
and 11,12-dihydroindolo2,3-a!carbazole, said aryl halide is an aryl 
iodide, said copper catalyst is selected from the group consisting of 
copper powder, copper (I) oxide, copper (I) chloride, copper (II) sulfate, 
copper (II) acetate, and a copper compound salt, and a ligand selected 
from the group consisting of monodentate tertiary amines and bidentate 
tertiary amines; a member wherein said indolocarbazole is 
5,11-di-m-tolyl-5,11-dihydroindolo3,2-b!carbazole, 
5,11-bis(3,4-dimethylphenyl)-5,11-dihydroindolo3,2-b!carbazole, 
5,11-di-1-naphthyl-5,11-dihydroindolo3,2-b!carbazole, 
5,11-diphenyl-5,11-dihydroindolo3,2-b!carbazole, 
5,11-bis-(1,1-biphenyl-4-yl)-5,11-dihydroindolo3,2-b!carbazole, 
5,11-bis(3-methoxyphenyl)-5,11-dihydroindolo3,2-b!carbazole, 
5,11-bis(4-chlorophenyl)-5,11-dihydroindolo3,2-b!carbazole, 
5,11-bis4'-(3-methyldiphenylamino)-1,1'-biphenyl-4-yl!-5,11-dihydroindolo 
3,2-b!carbazole, 
5,11-bis4'-(4-methyldiphenylamino)-1,1'-biphenyl-4-yl!-5,11-dihydroindolo 
3,2-b!carbazole, 
5,11-bis4'-(diphenylamino)-1,1'-biphenyl-4-yl!-5,11-dihydroindolo3,2-b!c 
arbazole, 
5,11-bis4'-(diphenylamino)-1,1'-biphenyl-4-yl!-5,11-dihydroindolo3,2-b!c 
arbazole, 
5,11-bis4'-(di-p-tolylamino)-1,1'-biphenyl-4-yl!-5,11-dihydroindolo3,2-b 
!carbazole, 
5,11-bis4'-(3,4-dimethyldiphenylamino)-1,1'-biphenyl-4-yl!-5,11-dihydroin 
dolo3,2-b!carbazole, 
5,11-bis4'-(3-methoxydiphenylamino)-1,1'-biphenyl-4-yl!-5,11-dihydroindol 
o3,2-b!carbazole, 
5,11-bis4'-(3-chlorodiphenylamino)-1,1'-biphenyl-4-yl!-5,11-dihydroindolo 
3,2-b!carbazole, 
5,11-bis4'-(4-chlorodiphenylamino)-1,1'-biphenyl-4-yl!-5,11-dihydroindolo 
3,2-b!carbazole, 
5,11-bis4'-(diphenylamino)-1,1'-biphenyl-4-yl!-2,8-dimethyl-5,11-dihydroi 
ndolo3,2-b!carbazole, 
5,11-bis4'-(4-methyldiphenylamino)-1,1'-biphenyl-4-yl!-2,8-dimethyl-5,11- 
dihydroindolo3,2-b!carbazole, 
5,11-bis4-(diphenylamino)phenyl!-5,11-dihydroindolo3,2-b!carbazole, 
5,11-bis4-(3-methyldiphenylamino)phenyl!-5,11-dihydroindolo3,2-b!carbazo 
le, 
5,11-bis4-(4-methyldiphenylamino)phenyl!-5,11-dihydroindolo3,2-b!carbazo 
le, 
5,11-bis4-(diphenylamino)phenyl!-2,8-dimethyl-5,11-dihydroindolo3,2-b!ca 
rbazole, 
5,11-bis4-(4-methyldiphenylamino)phenyl!-2,8-dimethyl-5,11-dihydroindolo 
3,2-b!carbazole, 
5,11-bis4-(1-naphthylphenylamino)phenyl!-5,11-dihydroindolo3,2-b!carbazo 
le, 5,7-di-m-tolyl-5,7-dihydroindolo2,3-b!carbazole, 
5,7-bis(3,4-dimethylphenyl)-5,7-dihydroindolo2,3-b!carbazole, 
5,7-di-1-naphthyl-5,7-dihydroindolo2,3-b!carbazole, 
5,7-diphenyl-5,7-dihydroindolo2,3-b!carbazole, 
5,7-bis-(1,1-biphenyl-4-yl)-5,7-dihydroindolo 2,3-b!carbazole, 
5,7-bis(3-methoxyphenyl)-5,7-dihydroindolo2,3-b!carbazole, 
5,7-bis4'-(3-methyldiphenylamino)-1,1'-biphenyl-4-yl!-5,7-dihydroindolo2 
,3-b!carbazole, 
5,7-bis4'-(diphenylamino)-1,1'-biphenyl-4-yl!-5,7-dihydroindolo2,3-b!car 
bazole, 5,7-bis4'-(di-p-tolylamino)-1-1'-biphenyl 
-4-yl!-5,7-dihydroindolo2,3-b!carbazole, 
5,7-bis4'-(diphenylamino)-1,1'-biphenyl-4-yl!-2,10-dimethyl-5,7-dihydroin 
dolo2,3-b!carbazole, 
5,7-bis4-(diphenylamino)phenyl!-5,7-dihydroindolo2,3-b!carbazole, 
5,7-bis4-(3-methyldiphenylamino)phenyl!-5,7-dihydroindolo2,3-b!carbazole 
, 5,8-diphenyl-5,8-dihydroindolo2,3-c!carbazole, 
5,8-di-m-tolyl-5,8-dihydroindolo2,3-c!carbazole, 
5,8-bis-(1,1-biphenyl-4-yl)-5,8-dihydroindolo2,3-c!carbazole, 
5,8-di-1-naphthyl-5,8-dihydroindolo2,3-c!carbazole, 
5,8-bis-4-(3-methyldiphenylamino)phenyl!-5,8-dihydroindolo2,3-c!carbazol 
e, 
5,8-bis4'-(3-methyldiphenylamino)-1,1'-biphenyl-4-yl!-5,8-dihydroindolo2 
,3-c!carbazole, 5,10-diphenyl-5,10-dihydroindolo3,2-a!carbazole, 
5,10-di-m-tolyl-5,10-dihydroindolo3,2-a!carbazole, 
5,10-bis-(1,1-biphenyl-4-yl)-5,10-dihydroindolo3,2-a!carbazole, 
5,10-di-1-naphthyl-5,10-dihydroindolo3,2-a!carbazole, 
5,10-bis-4-(3-methyldiphenylamino)phenyl!-5,10-dihydroindolo3,2-a!carbaz 
ole, 5,12-diphenyl-5,12-dihydroindolo3,2-c!carbazole, 
5,12-di-m-tolyl-5,12-dihydroindolo3,2-c!carbazole, 
5,12-bis-(1,1-biphenyl-4-yl)-5,12-dihydroindolo3,2-c!carbazole, 
5,12-di-1-naphthyl-5,12-dihydroindolo3,2-c!carbazole, 
5,12-bis-4-(3-methyldiphenylamino)phenyl!-5,12-dihydroindolo3,2-c!carbaz 
ole, 
5,12-bis4'-(3-methyldiphenylamino)-1,1'-biphenyl-4-yl!-5,12-dihydroindolo 
3,2-c!carbazole, 11,12-diphenyl-11,12-dihydroindolo2,3-a!carbazole, 
11,12-di-m-tolyl-11,12-dihydroindolo2,3-a!carbazole, 
11,12-di-p-tolyl-11,12-dihydroindolo2,3-a!carbazole, 
(3-methoxyphenyl)-5,7-dihydroindolo2,3-b!carbazole, 
5,7-bis4'-(3-methyldiphenylamino)-1,1'-biphenyl-4-yl!-5,7-dihydroindolo2 
,3-b!carbazole, 
5,7-bis4'-(diphenylamino)-1,1'-biphenyl-4-yl!-5,7-dihydroindolo2,3-b!car 
bazole, 
5,7-bis4'-(di-p-tolylamino)-1,1'-biphenyl-4-yl!-5,7-dihydroindolo2,3-b!c 
arbazole, 
5,7-bis4'-(diphenylamino)-1,1'-biphenyl-4-yl!-2,10-dimethyl-5,7-dihydroin 
dolo2,3-b!carbazole, 
5,7-bis4-(diphenylamino)phenyl!-5,7-dihydroindolo2,3-b!carbazole, 
5,7-bis4-(3-methyldiphenylamino)phenyl!-5,7-dihydroindolo2,3-b!carbazole 
, 5,8-diphenyl-5,8-dihydroindolo2,3-c!carbazole, 
5,8-di-m-tolyl-5,8-dihydroindolo2,3-c!carbazole, 
5,8-bis-(1,1-biphenyl-4-yl)-5,8-dihydroindolo2,3-c!carbazole, 
5,8-di-1-naphthyl-5,8-dihydroindolo2,3-c!carbazole, 
5,8-bis-4-(3-methyldiphenylamino)phenyl!-5,8-dihydroindolo2,3-c!carbazol 
e, 
5,8-bis4'-(3-methyldiphenylamino)-1,1'-biphenyl-4-yl!-5,8-dihydroindolo2 
,3-c!carbazole, 5,10-diphenyl-5,10-dihydroindolo3,2-a!carbazole, 
5,10-di-m-tolyl-5,10-dihydroindolo3,2-a!carbazole, 
5,10-bis-(1,1-biphenyl-4-yl)-5,10-dihydroindolo3,2-a!carbazole, 
5,10-di-1-naphthyl-5,10-dihydroindolo3,2-a!carbazole, 
5,10-bis-4-(3-methyldiphenylamino)phenyl!-5,10-dihydroindolo3,2-a!carbaz 
ole 5,12-diphenyl-5,12-dihydroindolo3,2-c!carbazole, 
5,12-di-m-tolyl-5,12-dihydroindolo3,2-c!carbazole, 
5,12-bis-(1,1-biphenyl-4-yl)-5,12-dihydroindolo3,2-c!carbazole, 
5,12-di-1-naphthyl-5,12-dihydroindolo3,2-c!carbazole, 
5,12-bis-4-(3-methyldiphenylamino)phenyl!-5,12-dihydroindolo3,2-c!carbaz 
ole, 
5,12-bis4'-(3-methyldiphenylamino)-1,1'-biphenyl-4-yl!-5,12-dihydroindolo 
3,2-c!carbazole, 11,12-diphenyl-11,12-dihydroindolo2,3-a!carbazole, or 
11,12-di-p-tolyl-11,12-dihydroindolo2,3-a!carbazole; and an imaging 
member wherein the supporting substrate is comprised of a conductive 
substrate, or a polymer, the photogenerator layer has a thickness of from 
about 0.05 to about 10 microns, the indolocarbazole transport layer has a 
thickness of from about 5 to about 30 microns, and wherein the 
photogenerating layer components are optionally dispersed in a resinous 
binder in an amount of from about 5 percent by weight to about 95 percent 
by weight; a photoconductive imaging member comprised of a supporting 
substrate, a photogenerating layer, and a charge transport layer, and 
wherein said charge transport layer is comprised of an indolocarbazole 
represented by the Formulas (Ia), (IIa), (IlIa), (IVa), (Va), or (VIa): 
##STR5## 
wherein R and R' are independently selected from the group consisting of a 
hydrogen atom, a halogen atom, alkyl, alkoxyl, and aryl; m and n are 
numbers; R.sup.1 and R.sup.2 are independently selected from the group 
consisting of alkyl, aryl, and diarylaminoaryl; R.sup.3 and R.sup.4 are an 
atom of hydrogen, alkyl, alkoxy, aryl, or halogen, and p is a number. 
Embodiments of the present invention include a method of imaging which 
comprises generating an electrostatic latent image on the imaging member 
comprised in the following order of a supporting substrate, a 
photogenerator layer, and an indolocarbazole of the formulas illustrated 
herein; developing the latent image; and transferring the developed 
electrostatic image to a suitable substrate; and wherein the imaging 
member is exposed to light of a wavelength of from about 400 to about 800 
nanometers. 
The imaging members of the present invention can in embodiments be prepared 
by a number of known methods, the process parameters and the order of 
coating of the layers being dependent, for example, on the member desired. 
The photogenerating and charge transport layers of the imaging members can 
be coated as solutions or dispersions onto a selective substrate by the 
use of a spray coater, dip coater, extrusion coater, roller coater, 
wire-bar coater, slot coater, doctor blade coater, gravure coater, and the 
like; and dried at from 40.degree. to about 200.degree. C. for from 10 
minutes to several hours under stationary conditions or in an air flow. 
The coating can be accomplished to provide a final coating thickness of 
from about 0.01 to about 30 microns after drying. The fabrication 
conditions for a given photoconductive layer can be tailored to achieve 
optimum performance and cost in the final members. 
Examples of substrate layers selected for the imaging members of the 
present invention can be opaque or substantially transparent, and may 
comprise any suitable material having the requisite mechanical properties. 
Thus, the substrate may comprise a layer of insulating material including 
inorganic or organic polymeric materials, such as MYLAR.RTM. a 
commercially available polymer, MYLAR.RTM. containing titanium, a layer of 
an organic or inorganic material having a semiconductive surface layer, 
such as indium tin oxide, or aluminum arranged thereon, or a conductive 
material inclusive of aluminum, chromium, nickel, brass or the like. The 
substrate may be flexible, seamless, or rigid, and many have a number of 
many different configurations, such as for example a plate, a cylindrical 
drum, a scroll, an endless flexible belt, and the like. In one embodiment, 
the substrate is in the form of a seamless flexible belt. In some 
situations, it may be desirable to coat on the back of the substrate, 
particularly when the substrate is a flexible organic polymeric material, 
an anticurl layer, such as for example polycarbonate materials 
commercially available as MAKROLON.RTM.. 
The thickness of the substrate layer depends on many factors, including 
economical considerations, thus this layer may be of substantial 
thickness, for example over 3,000 microns, or of minimum thickness 
providing there are no adverse effects on the system. In embodiments, the 
thickness of this layer is from about 75 microns to about 300 microns. 
Generally, the thickness of the photogenerator layers depends on a number 
of factors, including the thicknesses of the other layers and the amount 
of photogenerator material contained in these layers. Accordingly, this 
layer can be of a thickness of, for example, from about 0.05 micron to 
about 15 microns, and more specifically, from about 0.25 micron to about 1 
micron when, for example, each of the photogenerator compositions, or 
pigments is present in an amount of from about 30 to about 75 percent by 
volume. The maximum thickness of the layers in an embodiment is dependent 
primarily upon factors, such as photosensitivity, electrical properties 
and mechanical considerations. The photogenerating layer binder resin, 
optionally present in various suitable amounts, for example from about 1 
to about 20, and more specifically, from about 1 to about 10 weight 
percent, may be selected from a number of known polymers, such as 
poly(vinyl butyral), poly(vinyl carbazole), polyesters, polycarbonates, 
poly(vinyl chloride), polyacrylates and methacrylates, copolymers of vinyl 
chloride and vinyl acetate, phenoxy resins, polyurethanes, poly(vinyl 
alcohol), polyacrylonitrile, polystyrene, and the like. In embodiments of 
the present invention, it is desirable to select a coating solvent that 
does not disturb or adversely effect the other previously coated layers of 
the device. Examples of solvents that can be selected for use as coating 
solvents for the photogenerator layers are ketones, alcohols, aromatic 
hydrocarbons, halogenated aliphatic hydrocarbons, ethers, amines, amides, 
esters, and the like. Specific examples are cyclohexanone, acetone, methyl 
ethyl ketone, methanol, ethanol, butanol, amyl alcohol, toluene, xylene, 
chlorobenzene, carbon tetrachloride, chloroform, methylene chloride, 
trichloroethylene, tetrahydrofuran, dioxane, diethyl ether, dimethyl 
formamide, dimethyl acetamide, butyl acetate, ethyl acetate, methoxyethyl 
acetate, and the like. 
The coating of the photogenerator layers in embodiments of the present 
invention can be accomplished with spray, dip or wire-bar methods such 
that the final dry thickness of the photogenerator layer is, for example, 
from about 0.01 to about 30 microns and preferably from about 0.1 to about 
15 microns after being dried at, for example, about 40.degree. C. to about 
150.degree. C. for about 5 to about 90 minutes. 
Illustrative examples of polymeric binder materials that can be selected 
for the photogenerator pigments are as indicated herein, and include those 
polymers as disclosed in U.S. Pat. No. 3,121,006, the disclosure of which 
is totally incorporated herein by reference. 
As optional adhesives usually in contact with the supporting substrate, 
there can be selected various known substances inclusive of polyesters, 
polyamides, poly(vinyl butyral), poly(vinyl alcohol), polyurethane and 
polyacrylonitrile. This layer is of a thickness of, for example, from 
about 0.001 micron to about 1 micron. Optionally, this layer may contain 
effective suitable amounts, for example from about 1 to about 10 weight 
percent, conductive and nonconductive particles, such as zinc oxide, 
titanium dioxide, silicon nitride, carbon black, and the like, to provide, 
for example, in embodiments of the present invention further desirable 
electrical and optical properties. 
Examples of the highly insulating and transparent polymer binder material 
for the transport layer include components, such as those described in 
U.S. Pat. No. 3,121,006, the disclosure of which is totally incorporated 
herein by reference. Specific examples of polymer binder materials include 
polycarbonates, acrylate polymers, vinyl polymers, cellulose polymers, 
polyesters, polysiloxanes, polyamides, polyurethanes and epoxies as well 
as block, random or alternating copolymers thereof. Preferred electrically 
inactive binders are comprised of polycarbonate resins having a molecular 
weight of from about 20,000 to about 100,000 with a molecular weight of 
from about 50,000 to about 100,000 being particularly preferred. 
Generally, the transport layer contains from about 10 to about 75 percent 
by weight of the charge transport material, and preferably from about 35 
percent to about 50 percent of this material. 
Also, included within the scope of the present invention are methods of 
imaging and printing with the photoresponsive devices illustrated herein. 
These methods generally involve the formation of an electrostatic latent 
image on the imaging member, followed by developing the image with a toner 
composition comprised, for example, of thermoplastic resin, colorant, such 
as pigment, charge additive, and surface additives, reference U.S. Pat. 
Nos. 4,560,635; 4,298,697 and 4,338,390, the disclosures of which are 
totally incorporated herein by reference, subsequently transferring the 
image to a suitable substrate, and permanently affixing the image thereto. 
In those environments wherein the device is to be used in a printing mode, 
the imaging method involves the same steps with the exception that the 
exposure step can be accomplished with a laser device or image bar. 
The indolocarbazole compounds selected for the charge transport layer are 
as illustrated by, for example, Formulas (Ia) through (VIa); or 
optionally, mixtures thereof 
##STR6## 
wherein R and R' are independently selected from the group consisting of 
hydrogen atoms, halogen atoms, such as chlorine, bromine, fluorine, or 
iodine, alkyl groups with, for example, 1 to about 25 carbon atoms, alkoxy 
groups with, for example, from 1 to about 25 carbon atoms, aryl groups 
with, for example, from 6 to about 30 carbon atoms, fused aromatic rings, 
such as benzo, and the like; m and n are preferably numbers of from 0 to 
4; R.sup.1 and R.sup.2 are independently alkyl, aryl, vinyl, 
diarylaminoaryl groups, and the like; R.sup.3 and R.sup.4 are 
independently hydrogen atom, alkyl, alkoxy, aryl groups, and halogen atom; 
and p is preferably a number of from 1 to 3. Specific examples of alkyl 
groups are methyl, ethyl, propyl, butyl, pentyl, hexyl, octyl, nonyl, 
cyclohexyl, cyclopentyl, and the like; illustrative examples of specific 
aryl groups, R.sup.1 and R.sup.2 include phenyl, tolyl, halophenyl, such 
as chlorophenyl, alkoxyphenyl, such as methoxyphenyl, naphthyl, 
biphenylyl, terphenyl, and the like; and specific examples of alkoxy 
groups include methoxy, ethoxy, propoxy, butoxy, pentoxy, and the like. 
Other known alkyl, alkoxy, and aryl can be selected in embodiments of the 
present invention. 
Specifically, the photoconductive imaging member of the present invention 
is comprised of an indolocarbazole represented by the alternative Formulas 
(Ia) through (VIa), wherein R and R' are independently selected from the 
group consisting of a hydrogen atom, a halogen atom, alkyl, alkoxy, and 
aryl; m and n are numbers of 0 to 4; R.sup.1 and R.sup.2 are independently 
selected from the group consisting of alkyl, aryl, and diarylaminoaryl 
groups; R.sup.3 and R.sup.4 are hydrogen atom, alkyl, alkoxy, aryl, or 
halogen atom, and p is a number of from 1 to 3. The indolocarbazole 
compounds possess a number of advantages as illustrated herein, inclusive 
of for example that they display excellent hole transporting capability, 
superior thermal stability, and they can also be vacuum deposited as thin 
film hole transport components. The indolocarbazoles when selected as hole 
transport components, greatly improve the operational performance and life 
span of the imaging member. 
Specific examples of aryl groups selected for R.sup.1 and R.sup.2 are as 
indicated herein, and include, for example, phenyl, biphenylyl, naphthyl, 
thienyl and the like, and their substituted derivatives with substituents, 
such as alkyl, alkoxy, aryl, and halogen atoms. Aminoaryl groups can also 
be selected for R.sup.1 and R.sup.2 and these groups can be represented by 
Formula (VII). 
##STR7## 
wherein A is an arylene; Ar.sup.1, Ar.sup.2 are aryl groups with from 
about 6 to about 30 carbon atoms independently selected from, for example, 
the group consisting of phenyl, tolyl, xylyl, halophenyl, such as 
chlorophenyl, alkoxyphenyl, naphthyl and the like. Illustrative examples 
of arylene groups include those with from about 7 to about 25 carbon 
atoms, such as 1,4-phenylene, 1,3-phenylene, 4,4'-biphenylene, 
3,4'-biphenylene, 1,4-naphthylene, 2,6-naphthylene, 1,5-naphthylene, 
4,4'-terphenylene, and substituted derivatives thereof with substituents 
of, for example, alkyl with 1 to about 5 carbon atoms, phenyl, and aryl 
with substituents of halogen atom, alkyl and alkoxy with 1 to about 12 
carbons, and the like. Illustrative arylenes are represented by the 
following formulas: 
##STR8## 
The indolocarbazole hole transport compounds (Ia) through (VIa), wherein 
R.sup.1 and R.sup.2 are aryl groups, can be prepared by Ullmann 
condensation of the corresponding dihydroindolocarbazole precursors 
selected from those represented by Formulas (Ib) through (VIb) with aryl 
halide in the presence of a copper catalyst, especially a ligand copper 
catalyst as illustrated in U.S. Pat. Nos. 5,723,669; 5,705,697; 5,723,671; 
and U.S. Pat. Nos. 5,538,829; 5,648,542; 5,654,482 and 5,648,539, the 
disclosures of each being totally incorporated herein by reference. 
Specific examples of dihydroindolocarbazoles, which can be readily 
obtained by known literature processes, are, for example, 
5,11-dihydroindolo3,2-b!carbazole, 5,7-dihydroindolo2,3-b!carbazole, 
5,12-dihydroindolo3,2-c!carbazole, 5,10-dihydroindolo3,2-a!carbazole, 
11,12-dihydroindolo2,3-a!carbazole, and the like. 
Illustrative examples of aryl halides that can be utilized for the Ullmann 
condensation are iodobenzene, 3-iodotoluene, 4-iodotoluene, 
4-iodo-1,2-xylene, 1-iodonaphthalene, 2-iodonaphthalene, 4-iodobiphenyl, 
4-iodo-4'-(3-methyldiphenylamino)-1,1'-biphenyl, 
4-iodo-4'-(diphenylamino)-1,1'-biphenyl, N,N-diphenyl-4-iodoaniline, 
N-phenyl-N-3-tolyl-4-iodoaniline, and the like. The Ullmann condensation 
is generally accomplished in an inert solvent, such as dodecane, 
tridecance, xylene, sulfolane, high boiling petroleum ethers with boiling 
point of, for example, over about 150.degree. C., and the like, at a 
reaction temperature ranging from 90.degree. C. to about 300.degree. C., 
and preferably from 150.degree. C. to 250.degree. C. Any copper catalysts 
suitable for Ullmann condensation, including copper powder, copper (I) 
oxide, copper (I) chloride, copper (II) sulfate, copper (II) acetate, and 
the like, may be employed for the process of the present invention. An 
effective molar ratio of the copper catalyst to the dihydroindolocarbazole 
compound ranges from about 0.01 to about 0.5. The condensation reaction 
can be greatly accelerated with a base, such as for example an alkaline 
metal hydroxide or carbonate including potassium hydroxide, potassium 
carbonate, sodium hydroxide, and the like. After the condensation, the 
reaction mixture is cooled down to about room temperature, and the product 
is isolated by known separation techniques such as, for example, by 
filtration and chromatography. The product is generally characterized by 
known analytical techniques such as IR and NMR. 
The indolocarbazole hole transport molecules may be utilized in many forms 
in various applications. For example, they can be used as thin films 
formed of one or more of thin films formed of one or more of the 
indolocarbazole compounds, or mixtures with other known hole transport 
materials, such as those based on triarylamines, reference for example 
U.S. Pat. No. 4,265,990. The films may be formed by many fabrication 
techniques, such as for example vacuum deposition, spin coating, or 
molecular beam epitaxy technique. In another application, as active hole 
transport components in a transport medium, the indolocarbazole hole 
transport compounds can be dispersed in a polymer matrix, or in a sol gel 
matrix. Any conventional polymers, such as polycarbonates, polyesters, or 
polyhydrocarbons, and inorganic polymers, may be employed as the matrix 
binders for these applications. 
Illustrative examples of specific indolocarbazole compounds as represented 
by Formulas (Ia) through (VIa), which can be selected for use in the 
photoconductive imaging members of the present invention, with the 
preferred ones being (1), (2), (3), (4), (7), (8), (11), (13), (19), (24), 
(25), (30), (36), (41), (43), (46), (48), (49), and 51, are: 
(1) 5,11-di-m-tolyl-5,11-dihydroindolo3,2-b!carbazole, 
(2) 5,11-bis(3,4-dimethylphenyl)-5,11-dihydroindolo3,2-b!carbazole, 
(3) 5,11-di-1-naphthyl-5,11-dihydroindolo3,2-b!carbazole, 
(4) 
5,11-bis4'-(3-methyldiphenylamino)-1,1'-biphenyl-4-yl!-5,11-dihydroindolo 
3,2-b!carbazole, 
(5) 5,11-diphenyl-5,11-dihydroindolo3,2-b!carbazole, 
(6) 5,11-bis-(1,1-biphenyl-4-yl)-5,11-dihydroindolo3,2-b!carbazole, 
(7) 5,11-bis(3-methoxyphenyl)-5,11-dihydroindolo3,2-b!carbazole, 
(8) 5,11-bis(4-chlorophenyl)-5,11-dihydroindolo3,2-b!carbazole, 
(9) 
5,11-bis4'-(4-methyldiphenylamino)-1,1'-biphenyl-4-yl!-5,11-dihydroindolo 
3,2-b!carbazole, 
(10) 
5,11-bis4'-(diphenylamino)-1,1'-biphenyl-4-yl!-5,11-dihydroindolo3,2-b!c 
arbazole, 
(11) 
5,11-bis4'-(di-p-tolylamino)-1,1'-biphenyl-4-yl!-5,11-dihydroindolo3,2-b 
!carbazole, 
(12) 
5,11-bis4'-(3,4-dimethyldiphenylamino)-1,1'-biphenyl-4-yl!-5,11-dihydroin 
dolo3,2-b!carbazole, 
(13) 
5,11-bis4'-(3-methoxydiphenylamino)-1,1'-biphenyl-4-yl!-5,11-dihydroindol 
o3,2-b!carbazole, 
(14) 
5,11-bis4'-(3-chlorodiphenylamino)-1,1'-biphenyl-4-yl!-5,11-dihydroindolo 
3,2-b!carbazole, 
(15) 
5,11-bis4'-(4-chlorodiphenylamino)-1,1'-biphenyl-4-yl!-5,11-dihydroindolo 
3,2-b!carbazole, 
(16) 
5,11-bis4'-(diphenylamino)-1,1'-biphenyl-4-yl!-2,8-dimethyl-5,11-dihydroi 
ndolo3,2-b!carbazole, 
(17) 
5,11-bis4'-(4-methyldiphenylamino)-1,1'-biphenyl-4-yl!-2,8-dimethyl-5,11- 
dihydroindolo3,2-b!carbazole, 
(18) 5,11-bis4-(diphenylamino)phenyl!-5,11-dihydroindolo3,2-b!carbazole, 
(19) 
5,11-bis4-(3-methyldiphenylamino)phenyl!-5,11-dihydroindolo3,2-b!carbazo 
le, 
(20) 
5,11-bis4-(4-methyldiphenylamino)phenyl!-5,11-dihydroindolo3,2-b!carbazo 
le, 
(21) 
5,11-bis4-(diphenylamino)phenyl!-2,8-dimethyl-5,11-dihydroindolo3,2-b!ca 
rbazole, 
(22) 
5,11-bis4-(4-methyldiphenylamino)phenyl!-2,8-dimethyl-5,11-dihydroindolo 
3,2-b!carbazole, 
(23) 
5,11-bis4-(1-naphthylphenylamino)phenyl!-5,11-dihydroindolo3,2-b!carbazo 
le, 
(24) 5,7-di-m-tolyl-5,7-dihydroindolo2,3-b!carbazole, 
(25) 5,7-bis(3,4-dimethylphenyl)-5,7-dihydroindolo2,3-b!carbazole, 
(26) 5,7-di-1-naphthyl-5,7-dihydroindolo2,3-b!carbazole, 
(27) 5,7-diphenyl-5,7-dihydroindolo2,3-b!carbazole, 
(28) 5,7-bis-(1,1-biphenyl-4-yl)-5,7-dihydroindolo2,3-b!carbazole, 
(29) 5,7-bis(3-methoxyphenyl)-5,7-dihydroindolo2,3-b!carbazole, 
(30) 
5,7-bis4'-(3-methyldiphenylamino)-1,1'-biphenyl-4-yl!-5,7-dihydroindolo2 
,3-b!carbazole, 
(31) 
5,7-bis4'-(diphenylamino)-1,1'-biphenyl-4-yl!-5,7-dihydroindolo2,3-b!car 
bazole, 
(32) 
5,7-bis4'-(di-p-tolylamino)-1,1'-biphenyl-4-yl!-5,7-dihydroindolo2,3-b!c 
arbazole, 
(33) 
5,7-bis4'-(diphenylamino)-1,1'-biphenyl-4-yl!-2,10-dimethyl-5,7-dihydroin 
dolo2,3-b!carbazole, 
(34) 5,7-bis4-(diphenylamino)phenyl!-5,7-dihydroindolo2,3-b!carbazole, 
(35) 
5,7-bis4-(3-methyldiphenylamino)phenyl!-5,7-dihydroindolo2,3-b!carbazole 
(36) 5,8-diphenyl-5,8-dihydroindolo2,3-c!carbazole, 
(37) 5,8-di-m-tolyl-5,8-dihydroindolo2,3-c!carbazole, 
(38) 5,8-bis-(1,1-biphenyl-4-yl)-5,8-dihydroindolo2,3-c!carbazole, 
(39) 5,8-di-1-naphthyl-5,8-dihydroindolo2,3-c!carbazole, 
(40) 
5,8-bis-4-(3-methyldiphenylamino)phenyl!-5,8-dihydroindolo2,3-c!carbazol 
e, 
(41) 
5,8-bis4'-(3-methyldiphenylamino)-1,1'-biphenyl-4-yl!-5,8-dihydroindolo2 
,3-c!carbazole, 
(42) 5,10-diphenyl-5,10-dihydroindolo3,2-a!carbazole, 
(43) 5,10-di-m-tolyl-5,10-dihydroindolo3,2-a!carbazole, 
(44) 5,10-bis-(1,1-biphenyl-4-yl)-5,10-dihydroindolo3,2-a!carbazole, 
(45) 5,10-di-1-naphthyl-5,10-dihydroindolo3,2-a!carbazole, 
(46) 
5,10-bis-4-(3-methyldiphenylamino)phenyl!-5,10-dihydroindolo3,2-a!carbaz 
ole 
(47) 5,12-diphenyl-5,12-dihydroindolo3,2-c!carbazole, 
(48) 5,12-di-m-tolyl-5,12-dihydroindolo3,2-c!carbazole, 
(49) 5,12-bis-(1,1-biphenyl-4-yl)-5,12-dihydroindolo3,2-c!carbazole, 
(50) 5,12-di-1-naphthyl-5,12-dihydroindolo3,2-c!carbazole, 
(51) 
5,12-bis-4-(3-methyldiphenylamino)phenyl!-5,12-dihydroindolo3,2-c!carbaz 
ole, 
(52) 
5,12-bis4'-(3-methyldiphenylamino)-1,1'-biphenyl-4-yl!-5,12-dihydroindolo 
3,2-c!carbazole 
(53) 11,12-diphenyl-11,12-dihydroindolo2,3-a!carbazole, 
(54) 11,12-di-m-tolyl-11,12-dihydroindolo2,3-a!carbazole, 
(55) 11,12-di-p-tolyl-11,12-dihydroindolo2,3-a!carbazole, and the like. 
The substituents, such as for example, R and R', can be positioned at 
various different appropriate locations on the aromatic components, like 
the benzene ring. 
The following Examples are provided.

EXAMPLE I 
Synthesis of 5,11-di-m-tolyl-5,11-dihydroindolo3,2-b!carbazole (1) 
Preparation of 5,11-dihydroindolo3,2-b!carbazole: In a 1.5 liter flask 
equipped with a mechanical stirrer and a condenser were added glacial 
acetic acid (100 milliliters) and concentrated sulfuric acid (20 
milliliters). Into this mixture, which was maintained at 10.degree. C. 
with an ice bath, was added powdered cyclohexane-1,4-dione 
bisphenylhydrazone (22.0 grams) in small portions with stirring. After the 
aforementioned addition, the ice bath was removed and the mixture was 
allowed to warm to 23.degree. C., and stirred for a further 10 minutes. 
Subsequently, the mixture was heated to about 65.degree. C. (Centigrade 
throughout) until an exothermic reaction occurred. The reaction mixture 
was cooled with an ice bath, and within 5 minutes a light brown solid was 
formed. The reaction mixture was allowed to remain at room temperature, 
about 25.degree. C., for about 18 hours, and filtered. The filtered cake 
was then washed with acetic acid, water, and then stirred in boiling 
methanol for 30 minutes before filtering and drying in vacuo for about 2 
to 5 hours to provide 7.2 grams of pure 5,11-dihydroindolo3,2-b!carbazole 
as pale yellow crystals. 
Preparation of 5,11-di-m-tolyl-5,11-dihydroindolo3,2-b!carbazole 
A 200-milliliter 3-necked round bottom flask equipped with a mechanical 
stirrer, reflux condenser, and argon inlet was purged with argon and then 
charged with 5,11-dihydroindolo3,2-b!carbazole (5.1 grams, 0.02 mol), 
3-iodotoluene (8.69 grams, 0.04 mol), copper sulfate pentahydrate (0.25 
gram, 1.0 mmol), potassium carbonate (5.52 grams, 0.04 mol), and 
n-tridecane (5.0 milliliters). Under an argon atmosphere, the reaction 
mixture was heated to about 250.degree. C. with a heating mantle and 
allowed to proceed at this temperature to completion in about 6 hours. The 
mixture was cooled to about 100.degree. C., and 100 milliliters of toluene 
and 15 milliliters of water were then added with vigorous stirring. The 
resulting two phase mixture was transferred into a separatory funnel and 
the layers separated. The organic phase, which contained the desired 
product, was washed with water, and treated with 25 grams of alumina under 
an argon atmosphere, and filtered. The filtrate was then evaporated and 
the residue was recrystallized from cyclohexane to provide 6.8 grams of 
pure, about 99.9 percent, 
5,11-di-m-tolyl-5,11-dihydroindolo-3,2-b!carbazole (1). 
IR (Kbr): 1,604, 1,588, 1,490, 1,475, 1,450, 1,321, 1,201, 1,153, 760, 745, 
701 cm.sup.-1. 
.sup.1 H-NMR (CDCl.sub.3): .delta. 2.51 (s), 7.18-7.59 (m), 8.05 (s), 8.12 
(d, J=8.5 Hz). 
EXAMPLE II 
Synthesis of 
5,11-di-bis(3,4-dimethylphenyl)-m-5,11-dihydroindolo3,2-b!carbazole (2) 
A 200-milliliter 3-necked round bottom flask equipped with a mechanical 
stirrer, reflux condenser, and argon inlet was purged with argon and then 
charged with 5,11-dihydroindolo3,2-b!carbazole (5.1 grams, 0.02 mol), 
3-iodotoluene (9.28 grams, 0.04 mol), copper sulfate pentahydrate (0.25 
gram, 1.0 mmol), potassium carbonate (5.52 grams, 0.04 mol), and 
n-tridecane (5.0 milliliters). Under an argon atmosphere, the reaction 
mixture was heated to about 250.degree. C. with a heating mantle and 
allowed to proceed at this temperature to completion in about 6 hours. The 
reaction mixture was cooled to about 100.degree. C., and 100 milliliters 
of toluene and 15 milliliters of water were then added with vigorous 
stirring. The resulting two phase mixture was transferred into a 
separatory funnel and the layers separated. The organic phase was washed 
with water, treated under argon with 25 grams of alumina, and filtered. 
The filtrate was evaporated and the residue was recrystallized from 
cyclohexane to provide 7.5 grams of pure, about 99.8 percent, 
5,11-di-bis(3,4-dimethylphenyl)-m-5,11-dihydroindolo3,2-b!carbazole (2). 
IR (Kbr): 1,614, 1,605, 1,511, 1,458, 1,445, 1,324, 1,241, 1,183, 851, 747, 
743 cm.sup.-1. 
.sup.1 H-NMR (CDCl.sub.3): .delta. 2.42 (s), 2.44 (s), 7.14 to 7.47 (m), 
8.03 (s), 8.12 (d, J=8.5 Hz). 
EXAMPLE III 
Synthesis of 5,11-di-1-naphthyl-5,11-dihydroindolo3,2-b!carbazole (3) 
A 200 milliliter 3-necked round bottom flask equipped with a mechanical 
stirrer, reflux condenser, and argon inlet was purged with argon and then 
charged with 5,11-dihydroindolo3,2-b!carbazole (5.1 grams, 0.02 mol), 
1-iodonaphthalene (10.16 grams, 0.04 mol), copper sulfate pentahydrate 
(0.25 gram, 1.0 mmol), potassium carbonate (5.52 grams, 0.04 mol), and 
n-tridecane (5.0 milliliters). Under an argon atmosphere, the reaction 
mixture was heated to about 250.degree. C. with a heating mantle and 
allowed to proceed at this temperature to completion in about 6 hours. The 
reaction mixture was cooled to about 100.degree. C., and 100 milliliters 
of toluene and 15 milliliters of water were then added with vigorous 
stirring for 30 minutes. The resulting two phase mixture was transferred 
into a separatory funnel and the layers separated. The organic phase which 
contains the desired product was washed with water, treated with 25 grams 
of alumina under an argon atmosphere, and filtered. The filtrate was then 
evaporated and the residue was recrystallized from toluene to provide 2.5 
grams of pure, about 99.9 percent, 
5,11-di-1-naphthyl-5,11-dihydroindolo3,2-b!carbazole (3). 
IR (Kbr): 1,612, 1,595, 1,576, 1,506, 1,476, 1,468, 1,450, 1,320, 1,293, 
1,235, 1,189, 1,147, 803, 775, 746 cm.sup.-1. 
.sup.1 H-NMR (CDCl.sub.3): .delta. 6.98 (d, J=8.5 Hz), 7.13 to 7.48 (m), 
7.54.about.7.62 (m), 7.71.about.7.80 (m), 8.0.about.8.15 (m). 
EXAMPLE IV 
Synthesis of 
5,11-bis4'-(3-methyldiphenylamino)-1,1'-biphenyl-4-yl!-5,11-dihydroindolo 
-3,2-b!carbazole (4) 
A 100 milliliter 3-necked round bottom flask equipped with a mechanical 
stirrer, reflux condenser, and argon inlet was purged with argon, and then 
charged with 5,11-dihydroindolo3,2-b!carbazole (1.65 grams, 6.45 mmol), 
4-iodo-4'-(3-methyldiphenylamino)-1,1'-biphenyl (7.1 grams, 15.5 mmol), 
copper sulfate pentahydrate (0.12 grams, 0.5 mmol), potassium carbonate 
(2.1 grams, 15.2 mmol), and n-tridecane (5.0 milliliters). Under an argon 
atmosphere, the reaction mixture was heated to about 250.degree. C. with a 
heating mantle and allowed to proceed at this temperature to completion in 
about 6 hours. The reaction mixture was cooled to 25.degree. C. to induce 
precipitation of reaction product. The solid product was filtered, washed 
with water, and filtered. The crude product was purified by column 
chromatography on alumina using hot toluene as an eluant to provide 3.45 
grams of pure, about 99.9 percent, 
5,11-bis4'-(3-methyldiphenylamino)-1,1'-biphenyl-4-yl!-5,11-dihydroindolo 
-3,2-b!carbazole (8). 
IR (Kbr): 1,598, 1,495, 1,450, 1,320, 1,291, 1,277, 1,232, 742, 695 
cm.sup.31 1. 
.sup.1 H-NMR (DMSO-d.sup.6 -CDCl.sub.3): .delta. 2.30 (s), 6.88.about.7.51 
(m), 7.66 (d, J=8.6 Hz), 7.76 (d, J=8.6 Hz), 7.93 (d, J=8.6 Hz), 7.99 (s), 
8.17 (s), 8.19 (d, J=8.6 Hz). 
EXAMPLE IV 
A photoconductive imaging member can be prepared by sequentially coating a 
photogenerator layer and a hole transport layer on a supporting substrate 
of a titanized MYLAR.RTM., which can be precoated with a thin 0.025 micron 
silane blocking layer and a thin 0.1 micron polyester adhesive layer. The 
photogenerating layer can be comprised of a number of photogenerating 
pigments, such as hydroxygallium phthalocyanine Type V. A dispersion of 
Type V hydroxygallium phthalocyanine (HOGaPC) can be prepared by milling 
0.125 gram of the Type V, and 0.125 gram of 
polystyrene-b-polyvinylpyridine in 9.0 grams of chlorobenzene in a 30 
milliliter glass bottle containing 70 grams of 1/8 inch stainless steel 
balls. The bottle is placed on a Norton roller mill operating at 300 rpm 
for 20 hours. The dispersion is then coated on the titanized MYLAR.RTM. 
substrate using 1 mil film applicator to form, it is believed, a 
photogenerator layer. The formed photogenerating layer HOGaPc is dried at 
135.degree. C. for 20 minutes to a final thickness of about 0.3 micron. 
A hole transporting layer solution can prepared by dissolving 3 grams of 
the indolocarbazole, such as those of the above Examples, and 3.5 grams of 
polycarbonate in 40 grams of dichloromethane. The solution was coated onto 
the HOGaPc generator layer using a 6 mil film applicator. The charge 
transporting layer thus obtained was dried at from 100.degree. C. to 
135.degree. C. and dried. 
The xerographic electrical properties of the imaging members can be 
determined by known means, including electrostatically charging the 
surfaces thereof with a corona discharge source until the surface 
potentials, as measured by a capacitively coupled probe attached to an 
electrometer, attained an initial value V.sub.0 , of about -800 volts. 
After resting for 0.5 second in the dark, the charged members can it is 
believed attained a surface potential of V.sub.ddp, dark development 
potential. The member, when exposed to light from a filtered Xenon lamp 
with a XBO 150 watt bulb, induced a photodischarge which resulted in a 
reduction of surface potential to a V.sub.bg value, background potential. 
The percent of photodischarge was calculated as 100.times.(V.sub.ddp 
-V.sub.bg)/V.sub.ddp. The desired wavelength and energy of the exposed 
light can be determined by the type of filters placed in front of the 
lamp. The monochromatic light photosensitivity was determined using a 
narrow band-pass filter. 
When exposing the charged imaging member with the hydroxygallium 
phthalocyanine and the charge transport of Example 1, 830 nanometers of 
light at an intensity of 10 ergs/cm.sup.2, a photodischarge of 75 percent 
may be observed. The imaging member was fully discharged when it was 
exposed to both 680 and 830 nanometers of light. 
Other modifications of the present invention will occur to those of 
ordinary skill in the art subsequent to a review of the present 
application. These modifications and equivalents thereof are intended to 
be included within the scope of the present invention.